{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-598a113173594a4f87467083f8ff9a33","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"65d964a80df045bdf8ad0c72dccd86bb9404709d73602b532e1364e4bae257ca","doi":"10.1038/nature11680","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-5b7d3ef09e7b4f65","route_slugs":["ord-598a113173594a4f87467083f8ff9a33-21a202bd4983","ord-598a113173594a4f87467083f8ff9a33-33811c701567","ord-598a113173594a4f87467083f8ff9a33-327e6f5a36ca","ord-598a113173594a4f87467083f8ff9a33-e735ff749982"],"reactant_slugs":["ord-compound-60ddc11b43bc54501f1a","ord-compound-1d8ce2a674e51f3a9614"],"product_slugs":["ord-compound-ff3c2fb85adf8406e815","ord-compound-e95d353166ce351613b0"],"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_100"},{"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":"ClC1=NN=C(OC)C=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1722-10-7"}],"amount":{"moles":{"value":250,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[Zn].O=S(O)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"39971-65-8"}],"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(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"355-42-0"}],"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":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"FC(F)(F)C1=CC(Cl)=NN=C1OC"},{"type":"CAS_NUMBER","value":"1416821-58-3"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":45}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(C1=CC(Br)=CN=C1C(F)(F)F)C"},{"type":"CAS_NUMBER","value":"1260664-97-8"}],"measurements":[{"analysis_key":"product_2_isolated","type":"YIELD","percentage":{"value":20}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_isolated":{"type":"WEIGHT","details":"isolated"},"product_2_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1038/nature11680"}}},"entities":[{"slug":"ord-compound-60ddc11b43bc54501f1a","name":"C5H5ClN2O · ORD XBJLKXOOHLLTPG-UHFFFAOYSA-N","smiles":"COc1ccc(Cl)nn1","inchi":"InChI=1S/C5H5ClN2O/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3","formula":"C5H5ClN2O"},{"slug":"ord-compound-1d8ce2a674e51f3a9614","name":"CHF3O2SZn · ORD YSNORGWKORDJSP-UHFFFAOYSA-N","smiles":"O=S(O)C(F)(F)F.[Zn]","inchi":"InChI=1S/CHF3O2S.Zn/c2-1(3,4)7(5)6;/h(H,5,6);","formula":"CHF3O2SZn"},{"slug":"ord-compound-ff3c2fb85adf8406e815","name":"C6H4ClF3N2O · ORD LITNBBZLCLZEMR-UHFFFAOYSA-N","smiles":"COc1nnc(Cl)cc1C(F)(F)F","inchi":"InChI=1S/C6H4ClF3N2O/c1-13-5-3(6(8,9)10)2-4(7)11-12-5/h2H,1H3","formula":"C6H4ClF3N2O"},{"slug":"ord-compound-e95d353166ce351613b0","name":"C8H5BrF3NO · ORD LJIMXIWOZUHRLI-UHFFFAOYSA-N","smiles":"CC(=O)c1cc(Br)cnc1C(F)(F)F","inchi":"InChI=1S/C8H5BrF3NO/c1-4(14)6-2-5(9)3-13-7(6)8(10,11)12/h2-3H,1H3","formula":"C8H5BrF3NO"}],"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"]}