{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0ee895cc6b304408a98aafaa9be5173d","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"b0ccec3c22b7d77aa67a890ec95abcf92be7686dfed5bc76f783d6e13ddd6e56","doi":"10.1038/nature11680","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-5b7d3ef09e7b4f65","route_slugs":["ord-0ee895cc6b304408a98aafaa9be5173d-eb922973f2b3","ord-0ee895cc6b304408a98aafaa9be5173d-14927dd569b9"],"reactant_slugs":["ord-compound-695ababfc777804258ca","ord-compound-c1d7fbe326072f4a6a9f"],"product_slugs":["ord-compound-19dfca4154db83e42c6d"],"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_85"},{"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=C1C2=C(N=CN2C)N(C(=O)N1CCCCC(=O)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"06.05.6493"}],"amount":{"moles":{"value":250,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[Zn].O=S(O)CF"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1416821-54-9"}],"amount":{"moles":{"value":500,"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":"FC=1C(F)=C(F)C(=C(F)C1F)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"434-64-0"}],"amount":{"volume":{"value":986.1111,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}}},"outcomes":[{"reaction_time":{"value":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C1C2=C(N=C(N2C)CF)N(C(=O)N1CCCCC(=O)C)C"},{"type":"CAS_NUMBER","value":"1416821-85-6"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":75}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1038/nature11680"}}},"entities":[{"slug":"ord-compound-695ababfc777804258ca","name":"C13H18N4O3 · ORD BYPFEZZEUUWMEJ-UHFFFAOYSA-N","smiles":"CC(=O)CCCCn1c(=O)c2c(ncn2C)n(C)c1=O","inchi":"InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3","formula":"C13H18N4O3"},{"slug":"ord-compound-c1d7fbe326072f4a6a9f","name":"CH3FO2SZn · ORD HGWRELAVWVPFSN-UHFFFAOYSA-N","smiles":"O=S(O)CF.[Zn]","inchi":"InChI=1S/CH3FO2S.Zn/c2-1-5(3)4;/h1H2,(H,3,4);","formula":"CH3FO2SZn"},{"slug":"ord-compound-19dfca4154db83e42c6d","name":"C14H19FN4O3 · ORD XNXNAGUOJJAOBM-UHFFFAOYSA-N","smiles":"CC(=O)CCCCn1c(=O)c2c(nc(CF)n2C)n(C)c1=O","inchi":"InChI=1S/C14H19FN4O3/c1-9(20)6-4-5-7-19-13(21)11-12(18(3)14(19)22)16-10(8-15)17(11)2/h4-8H2,1-3H3","formula":"C14H19FN4O3"}],"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-5b7d3ef09e7b4f65","title":"Literature experiment — 10.1038/nature11680","source_type":"paper","doi":"10.1038/nature11680","url":"https://doi.org/10.1038/nature11680","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"]}