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Names | |||
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Preferred IUPAC name
2,3-Dihydro-1H-isoindole | |||
Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.156.955 | ||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
C8H9N | |||
Molar mass | 119.167 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. lenalidomide and pazinaclone.[3]
![](https://upload.wikimedia.org/wikipedia/commons/thumb/1/11/Lenalidomide_substructures.svg/220px-Lenalidomide_substructures.svg.png)
Substituted isoindolines
[edit]1-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
[edit]- 4,7-Dihydroisoindole
- Indole
- Indene
- Indoline
- Benzofuran
- Carbazole
- Carboline
- Isatin
- Methylindole
- Oxindole
- Pyrrole
- Skatole
- Benzene
References
[edit]- ^ Isoindoline
- ^ Isoindoline
- ^ 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
- ^ 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., DOI: 10.1039/C5OB00229J
- ^ A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization DOI: 10.1021/ol302987h
- ^ Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines DOI: 10.1039/B917246G