{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-2a9c2a07d2b64fddb079be1c83a3335a","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"775f91d0d48e0d2746f3c556969b0d041079e51b5ca26229f3ec1105abac8569","doi":"10.1038/nature11680","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-5b7d3ef09e7b4f65","route_slugs":["ord-2a9c2a07d2b64fddb079be1c83a3335a-035892b0a0ee","ord-2a9c2a07d2b64fddb079be1c83a3335a-62fce4ea172f"],"reactant_slugs":["ord-compound-86699cc690e5508fd47e","ord-compound-42d343cc9db844d2220b"],"product_slugs":["ord-compound-0fda148ef16639a8a122"],"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_76"},{"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":"N#CC1=NC=CC=N1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"14080-23-0"}],"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":"O=S(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-68-5"}],"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":"N#CC1=NC=C(C=N1)CC(F)(F)F"},{"type":"CAS_NUMBER","value":"1416821-71-0"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":21}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1038/nature11680"}}},"entities":[{"slug":"ord-compound-86699cc690e5508fd47e","name":"C5H3N3 · ORD IIHQNAXFIODVDU-UHFFFAOYSA-N","smiles":"N#Cc1ncccn1","inchi":"InChI=1S/C5H3N3/c6-4-5-7-2-1-3-8-5/h1-3H","formula":"C5H3N3"},{"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-0fda148ef16639a8a122","name":"C7H4F3N3 · ORD NCGWDYPCPLMFKO-UHFFFAOYSA-N","smiles":"N#Cc1ncc(CC(F)(F)F)cn1","inchi":"InChI=1S/C7H4F3N3/c8-7(9,10)1-5-3-12-6(2-11)13-4-5/h3-4H,1H2","formula":"C7H4F3N3"}],"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"]}