{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1a7798d251034c978b5f41b596d603bd","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"ae5a019c45510a46a915f9821eb8f48db553388474f3fa6abc67086243b5e8f5","doi":"10.1021/jacs.5b07154","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-05a85ade6785422e","route_slugs":["ord-1a7798d251034c978b5f41b596d603bd-55ec41695250","ord-1a7798d251034c978b5f41b596d603bd-9c13bc054a12"],"reactant_slugs":["ord-compound-89a4a2b4a299fc891ca5"],"product_slugs":["ord-compound-3dd013fb676f78e456f1","ord-compound-d44b3c52a206df84f7d8"],"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_1226"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-54-3"}],"amount":{"volume":{"value":69.9999,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC(C(=O)OC)CC1=CN(C=2C=CC=CC21)[Si](C(C)C)(C(C)C)C(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1803309-90-1"}],"amount":{"moles":{"value":21.1,"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":1.055,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=C2C=CC=3C=CC=NC3C12"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"66-71-7"}],"amount":{"moles":{"value":2.11,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":84.4,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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":5.275,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC(C(=O)OC)CC1=CN(C=2C=C(C=CC21)B3OC(C)(C)C(O3)(C)C)[Si](C(C)C)(C(C)C)C(C)C"},{"type":"CAS_NUMBER","value":"1803309-96-7"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":62}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC(C(=O)OC)CC1=CN(C=2C=CC(=CC21)B3OC(C)(C)C(O3)(C)C)[Si](C(C)C)(C(C)C)C(C)C"},{"type":"CAS_NUMBER","value":"1803310-04-4"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":8}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (500 MHz, CDCl3) δ 7.92 (s, 1H), 7.55 (d, J = 8.8 Hz, 1H), 7.51 (d, J = 8.8 Hz, 1H), 7.08 (s, 1H), 5.04 (d, J = 8.1 Hz, 1H), 4.65-4.63 (m, 1H), 3.62 (s, 3H); 3.27 (d, J = 5.5 Hz, 2H), 1.71-1.68 (m, 3H), 1.43 (s, J = 6.3 Hz, 9H), 1.35 (s, 12H), 1.13 (d, J = 7.2 Hz, 18H); 13C NMR (151 MHz, CDCl3) δ 172.7, 155.2, 141.0, 133.6, 131.4, 125.7, 121.0, 118.0, 113.5, 112.2, 83.5, 79.8, 54.3, 52.3, 28.5, 28.1, 25.0, 18.3, 13.0;"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1021/jacs.5b07154"}}},"entities":[{"slug":"ord-compound-89a4a2b4a299fc891ca5","name":"C26H42N2O4Si · ORD ZNSZNVYIQLMXSG-UHFFFAOYSA-N","smiles":"COC(=O)C(Cc1cn([Si](C(C)C)(C(C)C)C(C)C)c2ccccc12)NC(=O)OC(C)(C)C","inchi":"InChI=1S/C26H42N2O4Si/c1-17(2)33(18(3)4,19(5)6)28-16-20(21-13-11-12-14-23(21)28)15-22(24(29)31-10)27-25(30)32-26(7,8)9/h11-14,16-19,22H,15H2,1-10H3,(H,27,30)","formula":"C26H42N2O4Si"},{"slug":"ord-compound-3dd013fb676f78e456f1","name":"C32H53BN2O6Si · ORD WQYMWNHTXBROSP-UHFFFAOYSA-N","smiles":"COC(=O)C(Cc1cn([Si](C(C)C)(C(C)C)C(C)C)c2cc(B3OC(C)(C)C(C)(C)O3)ccc12)NC(=O)OC(C)(C)C","inchi":"InChI=1S/C32H53BN2O6Si/c1-20(2)42(21(3)4,22(5)6)35-19-23(17-26(28(36)38-14)34-29(37)39-30(7,8)9)25-16-15-24(18-27(25)35)33-40-31(10,11)32(12,13)41-33/h15-16,18-22,26H,17H2,1-14H3,(H,34,37)","formula":"C32H53BN2O6Si"},{"slug":"ord-compound-d44b3c52a206df84f7d8","name":"C32H53BN2O6Si · ORD NWFGWSSGLFLESF-UHFFFAOYSA-N","smiles":"COC(=O)C(Cc1cn([Si](C(C)C)(C(C)C)C(C)C)c2ccc(B3OC(C)(C)C(C)(C)O3)cc12)NC(=O)OC(C)(C)C","inchi":"InChI=1S/C32H53BN2O6Si/c1-20(2)42(21(3)4,22(5)6)35-19-23(17-26(28(36)38-14)34-29(37)39-30(7,8)9)25-18-24(15-16-27(25)35)33-40-31(10,11)32(12,13)41-33/h15-16,18-22,26H,17H2,1-14H3,(H,34,37)","formula":"C32H53BN2O6Si"}],"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-05a85ade6785422e","title":"Literature experiment — 10.1021/jacs.5b07154","source_type":"paper","doi":"10.1021/jacs.5b07154","url":"https://doi.org/10.1021/jacs.5b07154","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"]}