{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-e2e653bdc1fd49ccb37422bbc4fb7d61","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"d1cbad2eff686625511cbdaded1536e7defa31941f89508202e4807bd3c739b0","doi":"10.1038/nature11680","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-5b7d3ef09e7b4f65","route_slugs":["ord-e2e653bdc1fd49ccb37422bbc4fb7d61-3f69381a60da","ord-e2e653bdc1fd49ccb37422bbc4fb7d61-9344f2779565"],"reactant_slugs":["caffeine","ord-compound-42d343cc9db844d2220b"],"product_slugs":["ord-compound-2a5e0e113069dbd1704c"],"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_79"},{"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)N1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"58-08-2"}],"amount":{"moles":{"value":250,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[Zn].O=S(O)CC(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1416821-53-8"}],"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)CC(F)(F)F)N(C(=O)N1C)C"},{"type":"CAS_NUMBER","value":"1416821-65-2"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":51}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1038/nature11680"}}},"entities":[{"slug":"caffeine","name":"Caffeine","smiles":"CN1C=NC2=C1C(=O)N(C(=O)N2C)C","inchi":"InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3","formula":"C8H10N4O2"},{"slug":"ord-compound-42d343cc9db844d2220b","name":"C2H3F3O2SZn · ORD MPPCXQHXDLRDRL-UHFFFAOYSA-N","smiles":"O=S(O)CC(F)(F)F.[Zn]","inchi":"InChI=1S/C2H3F3O2S.Zn/c3-2(4,5)1-8(6)7;/h1H2,(H,6,7);","formula":"C2H3F3O2SZn"},{"slug":"ord-compound-2a5e0e113069dbd1704c","name":"C10H11F3N4O2 · ORD AHALIRHRLNWEHN-UHFFFAOYSA-N","smiles":"Cn1c(=O)c2c(nc(CC(F)(F)F)n2C)n(C)c1=O","inchi":"InChI=1S/C10H11F3N4O2/c1-15-5(4-10(11,12)13)14-7-6(15)8(18)17(3)9(19)16(7)2/h4H2,1-3H3","formula":"C10H11F3N4O2"}],"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"]}
