From 7e1b9f4040604bd0c939c17f7f1e03ca90e5887e Mon Sep 17 00:00:00 2001 From: ShaotingPeng <68555692+DrHermit@users.noreply.github.com> Date: Thu, 26 Mar 2026 18:26:09 +0400 Subject: [PATCH 1/4] Add files via upload --- ...ation of Decarboxylative Olefination.txtpb | 22082 ++++++++++++++ ...rning of Decarboxylative Olefination.txtpb | 25026 ++++++++++++++++ 2 files changed, 47108 insertions(+) create mode 100644 Bayesian Optimization of Decarboxylative Olefination.txtpb create mode 100644 Transfer Learning of Decarboxylative Olefination.txtpb diff --git a/Bayesian Optimization of Decarboxylative Olefination.txtpb b/Bayesian Optimization of Decarboxylative Olefination.txtpb new file mode 100644 index 0000000..006717b --- /dev/null +++ b/Bayesian Optimization of Decarboxylative Olefination.txtpb @@ -0,0 +1,22082 @@ +name: "Bayesian Optimization of Decarboxylative Olefination" +description: "A dataset of 120 experiments from Bayesian optimization on 5 distinct substrate combinations. The dataset can be used as training data for subsequent transfer learning opimization of similar decarboxylative olefinations between aldehydes and malonic acid derivatives." +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 68.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "4bc02d67f75c4980877bd8a93b42a491" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 79.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "74c7223c8e494c79b2f0b285938624d8" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 71.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "38cbaaca964e41888d059539687ed01f" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 71.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "40ddd0b632d34a51bf5b43126c91a6ce" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 13.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "6c7c9fd223fc44059a7a5aa04986b68c" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 68.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "57bc6a63120a489c837aa7cbbb9c3602" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: 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standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 39.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "d8fadeeb64d342f094947d6c7d18b98b" +} diff --git a/Transfer Learning of Decarboxylative Olefination.txtpb b/Transfer Learning of Decarboxylative Olefination.txtpb new file mode 100644 index 0000000..759c213 --- /dev/null +++ b/Transfer Learning of Decarboxylative Olefination.txtpb @@ -0,0 +1,25026 @@ +name: "Transfer Learning of Decarboxylative Olefination" +description: "The dataset of 136 experiments for the transfer learning optimization of 26 distinct substrate combinations. " +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } 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"auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "bf8c15eea111488e8bbb53dec070c3eb" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 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24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "2d25d0c8572f47cdaec4ec32d9856fa5" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 15.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "657aff0c0c744c42a41d68eb8c8e29fd" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "25d3c6f1b6c64e218b05c66b847a5858" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "03c886a4654d493faca4a19fad57bb15" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "34354ab62008468db2d5f3b0f2b8d905" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 44.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "0bf00cb2e29346d1b75de705e32643aa" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "0fd970367f6d454b84c262d7d380d182" +} From c9f7f5a5537f3cbc8479d558f80f40552bafa653 Mon Sep 17 00:00:00 2001 From: ShaotingPeng <68555692+DrHermit@users.noreply.github.com> Date: Fri, 3 Apr 2026 13:51:19 +0400 Subject: [PATCH 2/4] Add files via upload --- ...ecarboxylative olefination reactions.txtpb | 30482 ++++++++++++++ ...ecarboxylative olefination reactions.txtpb | 34546 ++++++++++++++++ 2 files changed, 65028 insertions(+) create mode 100644 Bayesian optimization of 5 decarboxylative olefination reactions.txtpb create mode 100644 Transfer Learning Optimization of 26 decarboxylative olefination reactions.txtpb diff --git a/Bayesian optimization of 5 decarboxylative olefination reactions.txtpb b/Bayesian optimization of 5 decarboxylative olefination reactions.txtpb new file mode 100644 index 0000000..55d2668 --- /dev/null +++ b/Bayesian optimization of 5 decarboxylative olefination reactions.txtpb @@ -0,0 +1,30482 @@ +name: "Bayesian optimization of 5 decarboxylative olefination reactions" +description: "The decarboxylative olefination between 5 pairings of aldehydes and malonic acid half-thioesters were studied in a Bayesian optimization campaign of 120 reaction datapoints. For each pairing, the catalyst, solvent, temperature and equivalents were optimized across 4 rounds of 6 experiments. Reactions performed by the Alan R. Healy group at New York University Abu Dhabi, and the pre-print publication is available on ChemRxiv at https://doi.org/10.26434/chemrxiv.15001213/v1. This dataset was used as training data for a subsequent transfer learning optimization of similar aldehydes and malonic acid derivatives (Dataset ID: )." +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE 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CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 68.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "2ee27ada16194210b7bda87dc94b3adf" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + 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volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 79.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "08fcda31e8274cc49c17c0d75510176b" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 71.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "40feafd1d54249eb90c6a5fbd4781c20" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + 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volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 71.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "e4637fb74be041e0960ce11adc5e8d4e" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } 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{ + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1D" + value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 13.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: 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details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: 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"Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } 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REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: 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+ } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2A" + value: "O=C(SCC)/C=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 42.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "4b013f39436a4dcea9fadae53c59acb7" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2A" + value: "O=C(SCC)/C=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 93.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "575113fb562b4cc1b84c3a2a434ec6f4" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + 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with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "10c6ac71445240dbbf338915447119a9" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of 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is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9e4fdcf5c67b4bb7ba971e7abd9cf6e6" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2A" + value: "O=C(SCC)/C=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 13.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "ee613671c857498b8e8ab2e4b4d273e8" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + 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"auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "77918e1a71894e8db89340b527c352e8" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + 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CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + 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details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: 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temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + 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"C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + 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+ person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "ad1e4c4c33774cee8d15c4c4ca077eb5" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2A" + value: "O=C(SCC)/C=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 67.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "0acd89f1f37d438a889c91797f947b45" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2A" + value: "O=C(SCC)/C=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 75.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "688a222b014843e7815a87da01c7ebd2" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "3C" + value: "F/C(C(SCC)=O)=C\\C1CCCCC1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 29.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9c9abcef01a0408f95cc2b1f7f3cd64f" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "3C" + value: "F/C(C(SCC)=O)=C\\C1CCCCC1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 65.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9e2b65b509d04616bb081d772f08bf7a" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + 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+ workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { 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"Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } 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{ + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + 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units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 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} + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of 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is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7f78a4c11fbb44608c03253262894628" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT 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FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in 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{ + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "f0bdbc7546e54d9f8fe7fe8172bc6134" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + 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DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: 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"sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "2c0e1a49a49441219fd234c68c50bbdf" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 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{ + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product 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{ + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9d7b0c32bc844e6faf61d9067d123407" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: 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"auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "6df15b85503e4e8da995c21f770cb915" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: 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{ + type: SMILES + details: "cyclohexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { 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"hydrocinnamaldehyde" + value: "[H]C(CCC1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(NC(C1=CC=CC=C1)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + 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"hydrocinnamaldehyde" + value: "[H]C(CCC1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(NC(C1=CC=CC=C1)=O)C(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: 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"O=C(SCC)/C(NC(C1=CC=CC=C1)=O)=C/CCC2=CC=CC=C2" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 82.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "3e51f8b737cc4012a19e369d4f460e88" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + 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moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "e05665c444004ceeb84295112c8837c2" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "6b2feda928724a7282aeb0cbc3570ea8" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + 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is_normalized: true + percentage { + value: 73.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "28f48bf2c5d84ae3af1b75f6c5089c47" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "dd9158073d5b48a09141649e6da0ce62" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" 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type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "c6228d2ffc8d409b9153fac1a5415e6b" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS 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ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal 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} + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of 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is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "8964ea4e7ba840d689c6c316a520e97c" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 46.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "ce0ff5b27bbf4d90b7f0e289fe9af4d8" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: 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"sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7094a9ce62f44a86bd598ff7e6340854" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 78.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "a2730e5c28bd4c36aaa7a8e76111f034" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: 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"10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7be3d3ff0804444caf8c1e8409b4a591" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: 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value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "6285e00548d44bc5a67d98c6a5fcc2b6" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: 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SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 48.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "61f5820ec01e4abcacd58781e5325ab2" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + 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"0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "749bfb88167b484b97d01fa74fc02726" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + 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type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + 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"C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 56.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "70ba9bc9c2624196802172bb12cd71fa" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 50.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "71027ba1afad4e6d9541e2b1119de856" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 70.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "027b7f59a8f349f7adc4e7e4c8f4a300" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 54.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "1f891b55a9374b239e6cb1f61f244845" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "CC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5B" + value: "C/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 39.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "e7544e16099840079401f1dbbca88f4a" +} diff --git a/Transfer Learning Optimization of 26 decarboxylative olefination reactions.txtpb b/Transfer Learning Optimization of 26 decarboxylative olefination reactions.txtpb new file mode 100644 index 0000000..dd8985d --- /dev/null +++ b/Transfer Learning Optimization of 26 decarboxylative olefination reactions.txtpb @@ -0,0 +1,34546 @@ +name: "Transfer Learning Optimization of 26 decarboxylative olefination reactions" +description: "The decarboxylative olefination between 26 pairings of aldehydes and malonic acid derivatives were studied in a transfer learning optimization campaign of 136 reaction datapoints. For each pairing, the catalyst, solvent, temperature and equivalents were optimized across several iterations of 2 experiments. Reactions performed by the Alan R. Healy group at New York University Abu Dhabi, and the pre-print publication is available on ChemRxiv at https://doi.org/10.26434/chemrxiv.15001213/v1. This transfer learning dataset was trained with the 120-experiment dataset generated from Bayesian optimization (Reaction ID)." +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "1A" + value: "O=C(SCC)/C=C/C1=CC=C([N+]([O-])=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 71.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "5cf8909ebe5046228e6181f706a1e53f" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: 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"7a17e013333844e4a3015b1ef5497466" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(OCC1=CC=CC=C1)C(O)=O" + } 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stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "5C" + value: "F/C(C(SCC)=O)=C\\C=C\\C1=CC=CC=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 63.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "fd6fe4afe7f6454c99a1c7f9d5a7c722" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: 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{ + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { 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25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: 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email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7b92c7c7a88143b59ef47c80ebd460dd" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: 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"The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + 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record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "09fef3b5fe95431ba70d042bc5958afa" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cinnamaldehyde" + value: "[H]C(/C=C/C1=CC=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: 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\302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + 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} + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + 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{ + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + 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email: "sp4767@nyu.edu" + } + } + } + reaction_id: "c8009b4d74244b47bd3e3bc4266bc5f7" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "3-acetylbenzaldehyde" + value: "[H]C(C1=CC(C(C)=O)=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: 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"a3f7d396338b4edaa41bdb3db8af007d" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "3-acetylbenzaldehyde" + value: "[H]C(C1=CC(C(C)=O)=CC=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)CC(O)=O" + } + 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type: SMILES + details: "furfural" + value: "O=C([H])C1=CC=CO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(SCC)C(OCC1=CC=CC=C1)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + 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} + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was 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false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 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details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "ClC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + 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value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "ClC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + 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"Cl/C(C(SCC)=O)=C\\C1=CC=C([N+]([O-])=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 5.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7b412c4f515342bd8ae695c5bf72f384" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "ClC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: 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"Cl/C(C(SCC)=O)=C\\C1=CC=C([N+]([O-])=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "e62bb51d3eba4deb9ef4606e270559c4" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" + value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "ClC(C(O)=O)C(SCC)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + 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"Cl/C(C(SCC)=O)=C\\C1=CC=C([N+]([O-])=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 60.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "4df608b7b440460a9683fc118ff4f877" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-nitrobenzaldehyde" 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amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { 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units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal 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is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + 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WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + 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REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: 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+ type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under 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units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 49.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "a201a5b14b5a4a73806db4579c0c6390" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 19.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "68810058c4644794a9d13541eacf90b3" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 82.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "d52a5fbe18114129a4db0ac0779da455" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)C" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2G" + value: "COC1=CC=C(/C=C(C)/C(OCC)=O)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "af1ba958139946ecbf3465635ae2a2ad" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OC)C(C(O)=O)Cl" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + 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"sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "2bbccb80638549afaff0d6556c2d053b" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OC)C(C(O)=O)Cl" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "2H" + value: "O=C(OC)/C(Cl)=C/C1=CC=C(OC)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 82.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "94dc3a0ba8f6466d8949ccf4fb760827" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OC)C(C(O)=O)Cl" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + 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time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "5ca12d74344a437a8460ebdcddba9b7e" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OC)C(C(O)=O)Cl" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + 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} + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9163df5694644102858cebbbafefe0b9" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + 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name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7842b0f4d84b487fa7334614097a6fae" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + 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+ email: "sp4767@nyu.edu" + } + } + } + reaction_id: "0ad0e15d8f824276ac9d749636e7e2ed" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cychexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(N(CC1=CC=CC=C1)CC2=CC=CC=C2)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "3I" + value: "O=C(N(CC1=CC=CC=C1)CC2=CC=CC=C2)/C=C/C3CCCCC3" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 31.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "5f7cb5bf3f954b2a8c9068070e49ba01" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cychexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(N(CC1=CC=CC=C1)CC2=CC=CC=C2)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a 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reaction_id: "4e96c00957a14bf0b22b75ba1b0df86d" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "cychexanecarboxaldehyde" + value: "[H]C(C1CCCCC1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: 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"4-methoxybenzaldehyde" + value: "[H]C(C1=CC=C(OC)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)F" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + 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amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(C(O)=O)F" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + 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SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(Cl)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "12K" + value: "O=C(OCC)/C(Cl)=C/C1=CC=C(I)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 80.0 + } + } + 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amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(Cl)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "12K" + value: "O=C(OCC)/C(Cl)=C/C1=CC=C(I)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 38.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "54358e64641244c9bd9700cabe68f896" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-iodobenzaldehyde" + value: "IC1=CC=C(C([H])=O)C=C1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(Cl)C(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "12K" + value: "O=C(OCC)/C(Cl)=C/C1=CC=C(I)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 82.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "81119e6d5c7b455e998334dd3614e52b" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-iodobenzaldehyde" + value: "IC1=CC=C(C([H])=O)C=C1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "Toluene" + value: "CC1=CC=CC=C1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "piperidine" + value: "C1CNCCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(OCC)C(Cl)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + 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carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "12K" + value: "O=C(OCC)/C(Cl)=C/C1=CC=C(I)C=C1" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 8.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "2435fba7e1244b16a631c26aa18a823c" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-trifluoromethylbenzaldehyde" + value: "[H]C(C1=CC=C(C(F)(F)F)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "morpholine" + value: "C1CNCCO1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(N(C)OC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + 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username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9e4959ef53674b73ad2f7d9159055257" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "4-trifluoromethylbenzaldehyde" + value: "[H]C(C1=CC=C(C(F)(F)F)C=C1)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "DMF" + value: "CN(C=O)C" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "BnNH2-TFA" + value: "NCC1=CC=CC=C1.O=C(C(F)(F)F)O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "O=C(N(C)OC)CC(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 50.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + 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"auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "9d5006bbf95845548f4af95a2a24116c" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "5-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde" + value: "FC1=CC=CC(COC2=C(Cl)C=C(NC3=C(C=C(C4=CC=C(C([H])=O)O4)C=C5)C5=NC=N3)C=C2)=C1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + 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{ + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "7cf49fd8ed5f4fbe83582927c00d9b6a" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "Aldehyde of 3-oxolithocholic acid" + value: "O=C1CC[C@@]2(C)[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4[C@@H](CCC([H])=O)C)([H])C1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + 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value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "c2388d4de46f4537a4799f31f3ef257f" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "Aldehyde of Indomethacin" + value: "ClC1=CC=C(C(N2C(C=CC(OC)=C3)=C3C(CC([H])=O)=C2C)=O)C=C1" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: 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celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 41.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "c8fa2f57cf7d412184e5f78422aae134" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "tert-butyl (2-oxoethyl)carbamate" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 14.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "53d96097657a444788482dba81f4389e" +} 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0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "86ea437e4ea14bdd9fa99e280742f3c0" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "tert-butyl (2-oxoethyl)carbamate" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "THF" + value: "C1COCC1" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.0 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.12 + units: MILLIMOLE + } + } + 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was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 44.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "b040b5bfa4ad49609406af69f0ca2892" +} +reactions { + inputs { + key: "Reaction Mixture" + value { + components { + identifiers { + type: SMILES + details: "tert-butyl (2-oxoethyl)carbamate" + value: "[H]C(CNC(OC(C)(C)C)=O)=O" + } + amount { + moles { + value: 0.1 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: true + } + components { + identifiers { + type: SMILES + details: "acetonitrile" + value: "CC#N" + } + amount { + volume { + value: 0.5 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + components { + identifiers { + type: SMILES + details: "DMAP" + value: "CN(C)c1ccncc1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: REAGENT + } + components { + identifiers { + type: SMILES + details: "pyrrolidine" + value: "C1CNCC1" + } + amount { + moles { + value: 0.01 + units: MILLIMOLE + } + } + reaction_role: CATALYST + } + components { + identifiers { + type: SMILES + value: "FC(C(SCC)=O)C(O)=O" + } + amount { + moles { + value: 0.2 + units: MILLIMOLE + } + } + reaction_role: REACTANT + is_limiting: false + } + components { + identifiers { + type: CAS_NUMBER + value: " 70955-01-0" + } + identifiers { + type: NAME + value: "4\303\205 Molecular Sieve" + } + amount { + mass { + value: 25.0 + units: MILLIGRAM + } + } + reaction_role: REAGENT + } + addition_order: 1 + } + } + setup { + vessel { + type: VIAL + material { + type: GLASS + } + volume { + value: 8.0 + units: MILLILITER + } + } + is_automated: false + environment { + type: FUME_HOOD + } + } + conditions { + temperature { + control { + type: DRY_ALUMINUM_PLATE + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: TEMPERATURE + details: "The product mixture was cooled to 25 \302\260C." + temperature { + control { + type: AMBIENT + } + setpoint { + value: 25.0 + units: CELSIUS + } + } + } + workups { + type: FILTRATION + details: "Filtered through a pad of celite" + keep_phase: "Organic" + is_automated: false + } + workups { + type: WASH + details: "\"The celite was washed with ethyl acetate (3 x 1 mL).\"" + input { + components { + identifiers { + type: SMILES + details: "ethyl acetate" + value: "CCOC(C)=O" + } + amount { + volume { + value: 3.0 + units: MILLILITER + } + } + reaction_role: WORKUP + } + } + } + workups { + type: CONCENTRATION + details: "The filtrate was concentrated under reduced pressure" + } + workups { + type: ADDITION + details: "A 0.07 M stock solution of the internal standard ethylene carbonate (0.70 mL in CDCl3) was added." + input { + components { + identifiers { + type: SMILES + details: "ethylene carbonate" + value: "O=C1OCCO1" + } + amount { + moles { + value: 0.05 + units: MILLIMOLE + } + } + reaction_role: INTERNAL_STANDARD + } + components { + identifiers { + type: SMILES + details: "CDCl3" + value: "[2H]C(Cl)(Cl)Cl" + } + amount { + volume { + value: 0.7 + units: MILLILITER + } + volume_includes_solutes: true + } + reaction_role: SOLVENT + } + } + } + outcomes { + reaction_time { + value: 24.0 + units: HOUR + } + products { + identifiers { + type: SMILES + details: "22C" + value: "F/C(C(SCC)=O)=C\\CNC(OC(C)(C)C)=O" + } + is_desired_product: true + measurements { + analysis_key: "1H NMR with internal standard" + type: YIELD + uses_internal_standard: true + is_normalized: true + percentage { + value: 0.0 + } + } + reaction_role: PRODUCT + } + analyses { + key: "1H NMR with internal standard" + value { + type: NMR_1H + is_of_isolated_species: false + } + } + } + provenance { + experimenter { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + doi: "10.26434/chemrxiv.15001213" + record_created { + time { + value: "2026-03-18T12:21:54" + } + person { + username: "auth0|69b6748d925a477aa3fd374a" + name: "sp4767@nyu.edu" + orcid: "0000-0002-7054-4914" + email: "sp4767@nyu.edu" + } + } + } + reaction_id: "cedb1d53940147a2be76fe2a1d09dc3f" +} From 99bfe416db4954ad8017c9a24a775fdb8aa8dcf6 Mon Sep 17 00:00:00 2001 From: ShaotingPeng <68555692+DrHermit@users.noreply.github.com> Date: Fri, 3 Apr 2026 13:54:55 +0400 Subject: [PATCH 3/4] Delete Bayesian Optimization of Decarboxylative Olefination.txtpb --- ...ation of Decarboxylative Olefination.txtpb | 22082 ---------------- 1 file changed, 22082 deletions(-) delete mode 100644 Bayesian Optimization of Decarboxylative Olefination.txtpb diff --git a/Bayesian Optimization of Decarboxylative Olefination.txtpb b/Bayesian Optimization of Decarboxylative Olefination.txtpb deleted file mode 100644 index 006717b..0000000 --- a/Bayesian Optimization of Decarboxylative Olefination.txtpb +++ /dev/null @@ -1,22082 +0,0 @@ -name: "Bayesian Optimization of Decarboxylative Olefination" -description: "A dataset of 120 experiments from Bayesian optimization on 5 distinct substrate combinations. The dataset can be used as training data for subsequent transfer learning opimization of similar decarboxylative olefinations between aldehydes and malonic acid derivatives." -reactions { - inputs { - key: "Reaction Mixture" - value { - components { - identifiers { - type: SMILES - details: "4-nitrobenzaldehyde" - value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" - } - amount { - moles { - value: 0.1 - units: MILLIMOLE - } - } - reaction_role: REACTANT - is_limiting: true - } - components { - identifiers { - type: SMILES - details: "acetonitrile" - value: "CC#N" - } - amount { - volume { - value: 0.5 - units: MILLILITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "DMAP" - value: "CN(C)c1ccncc1" - } - amount { - moles { - value: 0.0 - units: MILLIMOLE - } - } - } - components { - identifiers { - type: SMILES - details: "piperidine" - value: "C1CNCCC1" - } - amount { - moles { - value: 0.01 - units: MILLIMOLE - } - } - reaction_role: CATALYST - } - components { - identifiers { - type: SMILES - value: "O=C(SCC)C(C(O)=O)OCC1=CC=CC=C1" - } - amount { - moles { - value: 0.12 - units: MILLIMOLE - } - } - reaction_role: REACTANT - is_limiting: false - } - components { - identifiers { - type: SMILES - details: "ethylene carbonate" - value: "O=C1OCCO1" - } - amount { - moles { - value: 0.05 - units: MILLIMOLE - } - } - reaction_role: INTERNAL_STANDARD - } - components { - identifiers { - type: CAS_NUMBER - value: " 70955-01-0" - } - amount { - mass { - value: 25.0 - units: MILLIGRAM - } - } - reaction_role: REAGENT - } - addition_order: 1 - } - } - setup { - vessel { - type: VIAL - material { - type: GLASS - } - volume { - value: 8.0 - units: MILLILITER - } - } - is_automated: false - environment { - type: FUME_HOOD - } - } - conditions { - temperature { - control { - type: DRY_ALUMINUM_PLATE - } - setpoint { - value: 25.0 - units: CELSIUS - } - } - } - outcomes { - reaction_time { - value: 24.0 - units: HOUR - } - products { - identifiers { - type: SMILES - details: "1D" - value: "O=C(SCC)/C(OCC1=CC=CC=C1)=C/C2=CC=C([N+]([O-])=O)C=C2" - } - is_desired_product: true - measurements { - analysis_key: "1H NMR with internal standard" - type: YIELD - uses_internal_standard: true - is_normalized: true - percentage { - value: 68.0 - } - } - reaction_role: PRODUCT - } - analyses { - key: "1H NMR with internal standard" - value { - type: NMR_1H - is_of_isolated_species: false - } - } - } - provenance { - experimenter { - username: "auth0|69b6748d925a477aa3fd374a" - name: "sp4767@nyu.edu" - orcid: "0000-0002-7054-4914" - email: "sp4767@nyu.edu" - } - record_created { - time { - value: "2026-03-18T12:21:54" - } - person { - username: "auth0|69b6748d925a477aa3fd374a" - name: "sp4767@nyu.edu" - orcid: "0000-0002-7054-4914" - email: "sp4767@nyu.edu" - } - } - } - reaction_id: "4bc02d67f75c4980877bd8a93b42a491" -} -reactions { - inputs { - key: "Reaction Mixture" - value { - components { - identifiers { - type: SMILES - 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} - } - } - reaction_id: "40ddd0b632d34a51bf5b43126c91a6ce" -} -reactions { - inputs { - key: "Reaction Mixture" - value { - components { - identifiers { - type: SMILES - details: "4-nitrobenzaldehyde" - value: "[H]C(C1=CC=C([N+]([O-])=O)C=C1)=O" - } - amount { - moles { - value: 0.1 - units: MILLIMOLE - } - } - reaction_role: REACTANT - is_limiting: true - } - components { - identifiers { - type: SMILES - details: "acetonitrile" - value: "C1=CC=CC=C1" - } - amount { - volume { - value: 0.5 - units: MILLILITER - } - volume_includes_solutes: true - } - reaction_role: SOLVENT - } - components { - identifiers { - type: SMILES - details: "DMAP" - value: "CN(C)c1ccncc1" - } - amount { - moles { - value: 0.0 - units: MILLIMOLE - } - } - } - components { - identifiers { - type: SMILES - details: "piperidine" - value: "C1=CC=C(C=C1)CN.C(=O)(O)C(F)(F)F" - } - amount { - moles { - value: 0.01 - units: MILLIMOLE - } - } - reaction_role: CATALYST - } - components { - identifiers { - type: SMILES - 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