{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-52de714f0ca342bbb41f6b45117859e5","dataset_id":"ord_dataset-feaf1b793c6d408aaec1cac7cc3ceadc","reaction_class":"Minisci alkylation","transformation_sha256":"55cb3e63e2774118c4e1316427628c7c06fa5d68c7754183c0d283f6575603cd","doi":"10.1021/acs.orglett.8b02988","dataset_source_slug":"ord-dataset-feaf1b793c6d408aaec1cac7cc3ceadc","publication_source_slug":"ord-publication-975fc330cd328587","route_slugs":["ord-52de714f0ca342bbb41f6b45117859e5-3133d2c06b14","ord-52de714f0ca342bbb41f6b45117859e5-9393552081d3"],"reactant_slugs":["ord-compound-e047a7dab2e6d893e7e6","ord-compound-c2adbef3ce100b0193b2"],"product_slugs":["ord-compound-6e304974e634fa512825"],"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_3"},{"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=1C=2C=CC=CC2C=CC1C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"91-63-4"}],"amount":{"moles":{"value":3.5,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"startingmat_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(O)C1CCCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"98-89-5"}],"amount":{"moles":{"value":35,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)(O)OOS(=O)(=O)O.N"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7727-54-0"}],"amount":{"moles":{"value":10.5,"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":0.11669,"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":69.99883,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":40,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}}},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N=1C=2C=CC=CC2C(=CC1C)C3CCCCC3"},{"type":"CAS_NUMBER","value":"37597-46-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_isolated","type":"YIELD","percentage":{"value":78}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1HNMR (CDCl3, 300 MHz) δ 8.10 – 7.94 (2H, m, Ar‐H), 7.65 (1H, ddd, J=8.4, 6.8, 1.4 Hz, Ar‐H), 7.48 (1H,ddd, J=8.3, 6.8, 1.3 Hz, Ar‐H), 7.17 (1H, s, Ar‐H), 3.39 – 3.20 (1H, m, alkyl CH), 2.72 (3H, s, CH3), 2.08 – 1.80 (5H, m, alkyl CHs), 1.66 – 1.44 (4H, m, alkyl CHs), 1.41 – 1.28 (1H, m, alkyl CH); 13C NMR (75 MHz, CDCl3) δ 159.0, 153.4, 148.3, 129.7, 128.9, 125.4, 125.3, 123.0, 118.5, 38.9, 33.7, 27.1, 26.5,25.7"}}},"product_1_isolated":{"type":"WEIGHT","details":"isolated"}}}],"provenance":{"doi":"10.1021/acs.orglett.8b02988"}}},"entities":[{"slug":"ord-compound-e047a7dab2e6d893e7e6","name":"C10H9N · ORD SMUQFGGVLNAIOZ-UHFFFAOYSA-N","smiles":"Cc1ccc2ccccc2n1","inchi":"InChI=1S/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3","formula":"C10H9N"},{"slug":"ord-compound-c2adbef3ce100b0193b2","name":"C7H12O2 · ORD NZNMSOFKMUBTKW-UHFFFAOYSA-N","smiles":"O=C(O)C1CCCCC1","inchi":"InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)","formula":"C7H12O2"},{"slug":"ord-compound-6e304974e634fa512825","name":"C16H19N · ORD FUDPYOPZEFDRFK-UHFFFAOYSA-N","smiles":"Cc1cc(C2CCCCC2)c2ccccc2n1","inchi":"InChI=1S/C16H19N/c1-12-11-15(13-7-3-2-4-8-13)14-9-5-6-10-16(14)17-12/h5-6,9-11,13H,2-4,7-8H2,1H3","formula":"C16H19N"}],"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-975fc330cd328587","title":"Literature experiment — 10.1021/acs.orglett.8b02988","source_type":"paper","doi":"10.1021/acs.orglett.8b02988","url":"https://doi.org/10.1021/acs.orglett.8b02988","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"]}