82093-32-1

Basic information

• Product Name: 2-methylidene-3-oxocyclopentanecarbonitrile
• CAS NO: 82093-32-1
• Molecular Formula: C₇H₇NO
• Molecular Weight: 121.1366
• Mol File: 82093-32-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 282.5°C at 760 mmHg
• Flash Point: 124.7°C
• Density: 1.07g/cm³
• Vapor Pressure: 0.00334mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 2-methylidene-3-oxocyclopentanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylidene-3-oxocyclopentanecarbonitrile(82093-32-1)
• EPA Substance Registry System: 2-methylidene-3-oxocyclopentanecarbonitrile(82093-32-1)

Safety Data

• Hazardous Substances Data: 82093-32-1(Hazardous Substances Data)

Upstream product

• 110946-11-7 3-oxo 2-phenylsulfonylmethyl cyclopentane carbonitrile 
• 90380-01-1 3-oxo 2-phenylthiomethylcyclopentane carbonitrile 
• 73982-07-7 7-Cyano-1,4-dioxa-spiro[4.4]nonane-6-carboxylic acid methyl ester 
• 930-30-3 cyclopent-2-enone 
• 110921-43-2 3-oxo 2-phenylsulfinylmethyl cyclopentane 
• 82093-31-0 2-(hydroxymethylene)-3-cyanocyclopentanone ethylene ketal 
• 112496-86-3 2-methyl 3-oxo 1-cyclopentanecarbonitrile 
• 136584-01-5 3-trimethylsiloxy-2-cyclopentene-1-carbonitrile 

Relevant articles and documents

SYNTHESES OF NITRILE AND METHYL ESTER CORRESPONDING TO (dl)-SARKOMYCIN AND OF RELATED COMPOUNDS.

Nitrile 6a and ester 12 corresponding to (dl)-sarkomycin, 6- and 7-membered rings analogue nitriles 6b, 6c, and 3-methyl substituted nitrile 6d were prepared.Conjugate addition of cyanotrimethyl silane to cyclic α-enones gave 3-trimethylsiloxy 2-cycloalkene carbonitriles.Their alkylation with chloromethyl phenyl sulfide followed by oxone oxidation to sulfones and sulfinic acid elimination on basic alumina led to α-methylene carbonyl compounds.Obtention of the ester 12 involved acetalization of 3-oxo 2-phenylthiomethyl cyclopentane carbonitrile, basic hydrolysis into acid, deacetalization, esterification, oxidation and elimination of sulfinic acid.

Regiospecific Synthesis of Sarkomycin and Some Analogues

The first regiospecific total synthesis of the anticancer compound sarkomycin (1) is described.The starting material is 2-(carbomethoxycyclopent-2-enone (4), a useful precursor for cyclopentanoid natural products.The cyano derivative 5, the amide derivative 6, and the keto lactone 9 were also synthetized.The latter may be considered as a "cyclized" form of sarkomycin and was shown to open slowly to the natural product upon treament with dilute acid.