{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-24043f9eb4064b3b8242f778d5cc6992","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"6cfa28d1dd71c0ae4bf19920d71e3bcd6d123539806b4a64c672bf8044c783f3","doi":"10.1021/ja211422g","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-6eaca7b5b68c6594","route_slugs":["ord-24043f9eb4064b3b8242f778d5cc6992-3c943ddfbbc8","ord-24043f9eb4064b3b8242f778d5cc6992-48b54605b34f"],"reactant_slugs":["ord-compound-ffc31353796bcac3ece3","ord-compound-55d5b16ae3d85120a522"],"product_slugs":["ord-compound-1ba76df3dd16cf5a8bcf"],"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_50"},{"type":"CUSTOM","details":"rxn_tech from SURF table","value":"alkylation"},{"type":"REACTION_TYPE","details":"alkylation minisci","value":"alkylation minisci"}],"inputs":{"additive_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(O)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"76-05-1"}],"amount":{"moles":{"value":250,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[Zn].O=S(O)C(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1355729-38-2"}],"amount":{"moles":{"value":500,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CN=CC1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1122-54-9"}],"amount":{"moles":{"value":250,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OOC(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"75-91-2"}],"amount":{"moles":{"value":750,"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":402.77777,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"ClCCl"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"75-09-2"}],"amount":{"volume":{"value":986.1111,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"outcomes":[{"reaction_time":{"value":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(C=1C=CN=C(C1)C(F)F)C"},{"type":"CAS_NUMBER","value":"1256788-49-4"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":65}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1021/ja211422g"}}},"entities":[{"slug":"ord-compound-ffc31353796bcac3ece3","name":"C7H7NO · ORD WMQUKDQWMMOHSA-UHFFFAOYSA-N","smiles":"CC(=O)c1ccncc1","inchi":"InChI=1S/C7H7NO/c1-6(9)7-2-4-8-5-3-7/h2-5H,1H3","formula":"C7H7NO"},{"slug":"ord-compound-55d5b16ae3d85120a522","name":"CH2F2O2SZn · ORD RQZULCLQVHAIAM-UHFFFAOYSA-N","smiles":"O=S(O)C(F)F.[Zn]","inchi":"InChI=1S/CH2F2O2S.Zn/c2-1(3)6(4)5;/h1H,(H,4,5);","formula":"CH2F2O2SZn"},{"slug":"ord-compound-1ba76df3dd16cf5a8bcf","name":"C8H7F2NO · ORD TYLZKBGNHNAPDG-UHFFFAOYSA-N","smiles":"CC(=O)c1ccnc(C(F)F)c1","inchi":"InChI=1S/C8H7F2NO/c1-5(12)6-2-3-11-7(4-6)8(9)10/h2-4,8H,1H3","formula":"C8H7F2NO"}],"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-6eaca7b5b68c6594","title":"Literature experiment — 10.1021/ja211422g","source_type":"paper","doi":"10.1021/ja211422g","url":"https://doi.org/10.1021/ja211422g","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"]}
