{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-a62adabc2f494f2985e343f7aaaebc01","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"b718fb4cb4866fde2d610452465356eb4ff38cff1029f7d9e6a7e2fab322c794","doi":"10.1021/acs.orglett.8b02988","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-975fc330cd328587","route_slugs":["ord-a62adabc2f494f2985e343f7aaaebc01-6b23e3263b8f","ord-a62adabc2f494f2985e343f7aaaebc01-c71a96db326d"],"reactant_slugs":["ord-compound-38737ae630d25fc1e5fc","propanoic-acid"],"product_slugs":["ord-compound-0408e10f0a38b449701a"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lsf_lit_minisci_36"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C1C=C(C(=O)C=2C=CC=CC12)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"58-27-5"}],"amount":{"moles":{"value":0.15,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(O)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"79-09-4"}],"amount":{"moles":{"value":1.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)OOS(=O)(=O)O.N"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7727-54-0"}],"amount":{"moles":{"value":0.45,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7732-18-5"}],"amount":{"volume":{"value":0.005001,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"amount":{"volume":{"value":2.99995,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":40,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C1C=2C=CC=CC2C(=O)C(=C1C)CC"},{"type":"CAS_NUMBER","value":"2589-56-2"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":63}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1021/acs.orglett.8b02988"}}},"entities":[{"slug":"ord-compound-38737ae630d25fc1e5fc","name":"C11H8O2 · ORD MJVAVZPDRWSRRC-UHFFFAOYSA-N","smiles":"CC1=CC(=O)c2ccccc2C1=O","inchi":"InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3","formula":"C11H8O2"},{"slug":"propanoic-acid","name":"Propanoic acid","smiles":"CCC(=O)O","inchi":"InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)","formula":"C3H6O2"},{"slug":"ord-compound-0408e10f0a38b449701a","name":"C13H12O2 · ORD QWIBLPIAYFAQQQ-UHFFFAOYSA-N","smiles":"CCC1=C(C)C(=O)c2ccccc2C1=O","inchi":"InChI=1S/C13H12O2/c1-3-9-8(2)12(14)10-6-4-5-7-11(10)13(9)15/h4-7H,3H2,1-2H3","formula":"C13H12O2"}],"dataset":{"dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","name":"Minisci dataset from Roche","description":"Minisci reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":130,"path":"data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","sha256":"ebefbe9aba687f182d4f068e94be0f7fd71d1189bdb2eff2aca6fedf4d522bf3","bytes":37643,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/fe/ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc.parquet"},"publication":{"slug":"ord-publication-975fc330cd328587","title":"Literature experiment — 10.1021/acs.orglett.8b02988","source_type":"paper","doi":"10.1021/acs.orglett.8b02988","url":"https://doi.org/10.1021/acs.orglett.8b02988","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}
