{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-190a675c8ccc43a0837566a15ce408f6","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"2bb85c45b8f620e43c3488b69d979a61c12a54852795de0dc8f43731f40f4f93","doi":"10.1002/anie.201409186","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-e1a37b4fe2e07de6","route_slugs":["ord-190a675c8ccc43a0837566a15ce408f6-7b135d2d7fec"],"reactant_slugs":["ord-compound-8e9111441dc9a6c034f4"],"product_slugs":["ord-compound-b2d2cb20f0a324ea9085"],"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":"lit_pub_bo_800"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC1CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"132844-48-5"}],"amount":{"moles":{"value":1.3,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.0065,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":1.95,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=C(C(=C2C=CC3=C(N=CC(=C3C)C)C12)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1660-93-1"}],"amount":{"moles":{"value":0.013,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C1CCCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-82-7"}],"amount":{"volume":{"value":2.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"1f (200 mg, 1.3 mmol) and HBpin (0.28 mL, 1.9 mmol) were used. Purification was performed by MPLC (hexane/ethyl acetate = 10:1 to 3:1) to afford a mixture of 1f and 2f (NMR yield 2%). The mixture was purified again by MPLC (hexane/ethyl acetate = 6:1 to 3:2) to afford 2f as a white solid."},"outcomes":[{"reaction_time":{"value":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC1CC1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"1807546-55-9"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":2}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (600 MHz, CDCl3) δ 5.08 (brs, 1H), 3.11 (brs, 1H), 1.44 (s, 9H), 1.244 (s, 6H), 1.241 (s, 6H), 0.99 (brs, 1H), 0.65-0.63 (m, 1H), 0.22-0.18 (m, 1H).; 13C NMR (150 MHz, CDCl3) δ 156.5, 83.3, 79.0, 29.0, 28.4, 24.8, 24.6, 11.6, 0.1 (br)."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 282.1879","data":{"found":{"float_value":282.1879,"description":"Observed m/z"}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1002/anie.201409186"}}},"entities":[{"slug":"ord-compound-8e9111441dc9a6c034f4","name":"C8H15NO2 · ORD WFFGQLYKMWGXMU-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)NC1CC1","inchi":"InChI=1S/C8H15NO2/c1-8(2,3)11-7(10)9-6-4-5-6/h6H,4-5H2,1-3H3,(H,9,10)","formula":"C8H15NO2"},{"slug":"ord-compound-b2d2cb20f0a324ea9085","name":"C14H26BNO4 · ORD AQEITQBMKRPRMU-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)NC1CC1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C14H26BNO4/c1-12(2,3)18-11(17)16-10-8-9(10)15-19-13(4,5)14(6,7)20-15/h9-10H,8H2,1-7H3,(H,16,17)","formula":"C14H26BNO4"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation 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":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-e1a37b4fe2e07de6","title":"Literature experiment — 10.1002/anie.201409186","source_type":"paper","doi":"10.1002/anie.201409186","url":"https://doi.org/10.1002/anie.201409186","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"]}