| 词条 | Isoindoline |
| 释义 |
| verifiedrevid = 382025399 | ImageFileL1 = Isoindoline numbering.svg | ImageSizeL1 = | ImageFileR1 = Isoindoline3d.png | ImageSizeR1 = | ImageNameR1 = 3D representation of isoindoline | IUPACName = 2,3-dihydro-1H-isoindole | Section1 = {{Chembox Identifiers | CASNo = 496-12-8 | CASNo_Comment = [1] | PubChem = 422478 | ChemSpiderID = 373951 | SMILES = c1cccc2c1CNC2 | InChI = 1/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 | InChIKey = GWVMLCQWXVFZCN-UHFFFAOYAS | StdInChI = 1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 | StdInChIKey = GWVMLCQWXVFZCN-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C = 8 | H = 9 | N = 1 }}Isoindoline is a heterocyclic organic compound with the molecular formula C8H9N.[2] The parent compound has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound's structure is similar to indoline except that the nitrogen atom is in the 2 position instead of the 1 position of the five-membered ring. Isoindoline itself is not commonly encountered, but several derivatives are found in nature and some synthetic derivatives are commercially valuable drugs, e.g. pazinaclone.[3] Substituted isoindolines1-Substituted isoindolines and isoindolinones are chiral. Isoindolylcarboxylic acid and 1,3-disubstituted isoindolines are constituents of some pharmaceuticals and natural products. Isoindolines can be prepared by 1,2-addition of a nucleophile onto a bifunctional ε-benzoiminoenoates followed by intramolecular aza-Michael reaction. Another route involves [3+2] cycloaddition of the azomethine ylides (e.g. (CH2)2NR) to quinone in the presence of suitable catalysts. These methods have also been adapted to give chiral derivatives.[4][5][6] Related compounds
References1. ^Isoindoline 2. ^Isoindoline 3. ^Speck Klaus; Magauer Thomas "The chemistry of isoindole natural products" Beilstein journal of organic chemistry 2013, vol. 9, pp. 2048-78. {{doi|10.3762/bjoc.9.243}} 4. ^Pandey, G.; Varkhedkar, R.; Tiwari, D (2015) Efficient Access to Enantiopure 1,3-disubstituted Isoindolines from Selective Catalytic Fragmentation of Original Desymmetrized Rigid Overbred Template, Org. Biomol. Chem., 10.1039/C5OB00229J 5. ^A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization 10.1021/ol302987h 6. ^Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines 10.1039/B917246G 1 : Isoindolines |
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