{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-02943d791f4d471195f47a5b366e8b27","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"867102de14290e282c545f1fa771513f49d1d8122a6f5f5866476e74c81fd0e1","doi":"10.1038/nature11680","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-5b7d3ef09e7b4f65","route_slugs":["ord-02943d791f4d471195f47a5b366e8b27-1d57e06bc8ad","ord-02943d791f4d471195f47a5b366e8b27-969e99ac5601","ord-02943d791f4d471195f47a5b366e8b27-ddcff2a3a0ac","ord-02943d791f4d471195f47a5b366e8b27-e29fa263fcd4"],"reactant_slugs":["ord-compound-986fa26b8f4ef8507bf1","ord-compound-c1d7fbe326072f4a6a9f"],"product_slugs":["ord-compound-ab0aaedb7f33a0ddf086","ord-compound-168d4eda61f1f5f9a213"],"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_83"},{"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=C(OCC)C=1C=CN=CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1570-45-2"}],"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=C(OCC)C=1C=C(N=C(C1)CF)CF"},{"type":"CAS_NUMBER","value":"1416821-87-8"}],"measurements":[{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":69}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C=1C=CN=C(C1)CF"},{"type":"CAS_NUMBER","value":"1416821-86-7"}],"measurements":[{"analysis_key":"product_2_isolated","type":"YIELD","percentage":{"value":4}}],"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-986fa26b8f4ef8507bf1","name":"C8H9NO2 · ORD MCRPKBUFXAKDKI-UHFFFAOYSA-N","smiles":"CCOC(=O)c1ccncc1","inchi":"InChI=1S/C8H9NO2/c1-2-11-8(10)7-3-5-9-6-4-7/h3-6H,2H2,1H3","formula":"C8H9NO2"},{"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-ab0aaedb7f33a0ddf086","name":"C10H11F2NO2 · ORD CWABMTGQVGRLCK-UHFFFAOYSA-N","smiles":"CCOC(=O)c1cc(CF)nc(CF)c1","inchi":"InChI=1S/C10H11F2NO2/c1-2-15-10(14)7-3-8(5-11)13-9(4-7)6-12/h3-4H,2,5-6H2,1H3","formula":"C10H11F2NO2"},{"slug":"ord-compound-168d4eda61f1f5f9a213","name":"C9H10FNO2 · ORD AVDJSYVAJRQUNI-UHFFFAOYSA-N","smiles":"CCOC(=O)c1ccnc(CF)c1","inchi":"InChI=1S/C9H10FNO2/c1-2-13-9(12)7-3-4-11-8(5-7)6-10/h3-5H,2,6H2,1H3","formula":"C9H10FNO2"}],"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"]}