{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-011d03874e264f86867f1c58fbd301f2","dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","reaction_class":"Nickel-catalyzed cross-coupling","transformation_sha256":"e721314b15d34b914eafbf970a8498dfe03c1a2c5a274baafdf51b66850b570a","doi":"10.1021/acs.joc.6b00289","dataset_source_slug":"ord-dataset-9b8aa9a7835143ef8ce3f70abfab7545","publication_source_slug":"ord-publication-ee66505fa5a1e566","route_slugs":["ord-011d03874e264f86867f1c58fbd301f2-112dc262fd24","ord-011d03874e264f86867f1c58fbd301f2-2f54affefbb1"],"reactant_slugs":["ord-compound-41088ece3f292d735820","ord-compound-8b1d18ff1953732cb113"],"product_slugs":["ord-compound-dafba3ceb03668a0d12b"],"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.","Some source yields use float_value rather than a typed percentage; the original value is retained without asserting units.","At least one source reactant quantity is zero; no stoichiometric amount is inferred from this placeholder."],"raw":{"identifiers":[{"type":"REACTION_TYPE","value":"1940"}],"inputs":{"dcype":{"components":[{"identifiers":[{"type":"NAME","value":"dcype"}],"amount":{"moles":{"value":0.040000003,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"CC(C)OP(=O)OC(C)C":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)OP(=O)OC(C)C"},{"type":"NAME","value":"effective_coupling_partner"}],"amount":{"moles":{"value":0,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"CC(C)(C)C(=O)Oc1ccc(C#N)cc1":{"components":[{"identifiers":[{"type":"SMILES","value":"CC(C)(C)C(=O)Oc1ccc(C#N)cc1"},{"type":"NAME","value":"substrate"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":110,"units":"CELSIUS"}}},"outcomes":[{"reaction_time":{"value":46,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"CC(C)OP(=O)(OC(C)C)c1ccc(C#N)cc1"}],"is_desired_product":true,"measurements":[{"type":"YIELD","float_value":{"value":82}}],"reaction_role":"PRODUCT"}],"analyses":{"isolated_yield":{"type":"CUSTOM","details":"isolated yield"}}}],"provenance":{"doi":"10.1021/acs.joc.6b00289"}}},"entities":[{"slug":"ord-compound-41088ece3f292d735820","name":"C12H13NO2 · ORD KVCYRHCBMVONNS-UHFFFAOYSA-N","smiles":"CC(C)(C)C(=O)Oc1ccc(C#N)cc1","inchi":"InChI=1S/C12H13NO2/c1-12(2,3)11(14)15-10-6-4-9(8-13)5-7-10/h4-7H,1-3H3","formula":"C12H13NO2"},{"slug":"ord-compound-8b1d18ff1953732cb113","name":"C6H15O3P · ORD BLKXLEPPVDUHBY-UHFFFAOYSA-N","smiles":"CC(C)O[PH](=O)OC(C)C","inchi":"InChI=1S/C6H15O3P/c1-5(2)8-10(7)9-6(3)4/h5-6,10H,1-4H3","formula":"C6H15O3P"},{"slug":"ord-compound-dafba3ceb03668a0d12b","name":"C13H18NO3P · ORD RXINMJQMNDSCKD-UHFFFAOYSA-N","smiles":"CC(C)OP(=O)(OC(C)C)c1ccc(C#N)cc1","inchi":"InChI=1S/C13H18NO3P/c1-10(2)16-18(15,17-11(3)4)13-7-5-12(9-14)6-8-13/h5-8,10-11H,1-4H3","formula":"C13H18NO3P"}],"dataset":{"dataset_id":"ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545","name":"NiCOlit","description":"Nickel-catalyzed cross-couplings extracted from organic reaction publications","records_in_source":1762,"path":"data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","sha256":"195765643b4aaad79d9ed82de6737a4855b9f2716e0bc0aa10cff950b7604d39","bytes":126909,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/9b/ord_dataset-9b8aa9a7835143ef8ce3f70abfab7545.parquet"},"publication":{"slug":"ord-publication-ee66505fa5a1e566","title":"Literature experiment — 10.1021/acs.joc.6b00289","source_type":"paper","doi":"10.1021/acs.joc.6b00289","url":"https://doi.org/10.1021/acs.joc.6b00289","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"]}