{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-84a1619a2aaa485aa3d6761aec50cd2f","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"63eb4aae1f483d866375a08d43197e4e8fbd383c9085fe3151e4ebbdd15f64ed","doi":"10.1002/anie.201409186","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-e1a37b4fe2e07de6","route_slugs":["ord-84a1619a2aaa485aa3d6761aec50cd2f-56e0e56f4c16"],"reactant_slugs":["ord-compound-59a574b3287ba3366832"],"product_slugs":["ord-compound-b728f470b8300866bb39"],"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_801"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1CC1CCC)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1807546-51-5"}],"amount":{"moles":{"value":0.081,"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":0.000405,"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":0.1215,"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":0.00081,"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":0.1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"1j (15.0 mg, 81 µmol) and HBpin (17.8 µL, 0.12 mmol) were used. Purification was performed by MPLC (hexane/ethyl acetate = 9:1 to 7:3, then hexane/ether = 1:1 to 0:1), and finally by GPC to afford 5.9 mg of 2j as a colorless oil in a 23% yield. NOE was observed between H-1 and H-3 and not observed between H-1 and H-2. This result indicates that 2j has cis configuration between the N group and the B group"},"outcomes":[{"reaction_time":{"value":18,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1C(B2OC(C)(C)C(O2)(C)C)C1CCC)C(C)(C)C"},{"type":"CAS_NUMBER","value":"1807546-56-0"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":23}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (600 MHz, CDCl3) δ 6.58 (d, J= 6.0 Hz, 1H), 3.19-3.16 (m, 1H), 1.45-1.37 (m, 3H), 1.26-1.24 (m, 13H), 1.17 (s, 9H), 0.92-0.88 (m, 4H), 0.03 (dd, J= 7.8, 6.6 Hz, 1H).; 13C NMR (150 MHz, CDCl3) δ178.8, 83.4, 38.6, 35.3, 34.7, 27.4, 27.0, 25.0, 24.6, 22.0, 13.7, 6.7 (br)."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 310.2535","data":{"found":{"float_value":310.2535,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201409186"}}},"entities":[{"slug":"ord-compound-59a574b3287ba3366832","name":"C11H21NO · ORD GEVZQEQTRSXXME-UHFFFAOYSA-N","smiles":"CCCC1CC1NC(=O)C(C)(C)C","inchi":"InChI=1S/C11H21NO/c1-5-6-8-7-9(8)12-10(13)11(2,3)4/h8-9H,5-7H2,1-4H3,(H,12,13)","formula":"C11H21NO"},{"slug":"ord-compound-b728f470b8300866bb39","name":"C17H32BNO3 · ORD TYWYGKRFXLHFNU-UHFFFAOYSA-N","smiles":"CCCC1C(NC(=O)C(C)(C)C)C1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C17H32BNO3/c1-9-10-11-12(13(11)19-14(20)15(2,3)4)18-21-16(5,6)17(7,8)22-18/h11-13H,9-10H2,1-8H3,(H,19,20)","formula":"C17H32BNO3"}],"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"]}