92250-13-0

Basic information

• Product Name: 3-cyclohexyl-1,3-dihydro-indol-2-one
• Synonyms: 3-cyclohexyl-1,3-dihydro-indol-2-one
• CAS NO: 92250-13-0
• Molecular Formula: C₁₄H₁₇NO
• Molecular Weight: 215
• Mol File: 92250-13-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-cyclohexyl-1,3-dihydro-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-cyclohexyl-1,3-dihydro-indol-2-one(92250-13-0)
• EPA Substance Registry System: 3-cyclohexyl-1,3-dihydro-indol-2-one(92250-13-0)

Safety Data

• Hazardous Substances Data: 92250-13-0(Hazardous Substances Data)

Upstream product

• 100717-32-6 3-cyclohexyl-1H-indole 
• 3478-78-2 3-cyclohexylidene-1,3-dihydro-indol-2-one 
• 59-48-3 2-oxoindole 
• 108-94-1 cyclohexanone 
• 5292-21-7 Cyclohexylacetic acid 
• 613-94-5 benzoic acid hydrazide 
• 91-56-5 indole-2,3-dione 
• 108-93-0 cyclohexanol 

Downstream Products

• 140701-27-5 3-Bromo-3-cyclohexyl-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester 
• 185199-40-0 3-cyclohexyl-1,3-dimethyloxindole 
• 131609-15-9 5-(2-chloro-1-oxoethyl)-3-cyclohexyl-1,3-dihydro-2H-indol-2-one 
• 140701-21-9 3-Cyclohexyl-2-ethoxycarbonyloxy-indole-1-carboxylic acid ethyl ester 

Relevant articles and documents

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

C-Alkylation of Various Carbonucleophiles with Secondary Alcohols under CoIII-Catalysis

Oxindoles have been successfully α-alkylated under Cp*CoIII catalysis by a vast array of secondary alcohols, including cyclic, acyclic, symmetrical, and unsymmetrical, to produce C-alkylated oxindoles. This protocol was also extended to the α-alkylation of N,N-dimethyl barbituric acid and benzyl cyanides. The kinetic profile and other preliminary mechanistic investigations suggest a first-order reaction rate in oxindoles and catalysts. A plausible catalytic cycle is proposed on the basis of the kinetic profile, of other preliminary mechanistic investigations, and of previous mechanistic studies on similar transformations, whereas density functional theory calculations provide insight into the nature of the active species.

A Facile Method for the Synthesis of 3-Alkyloxindole

Benzylamine in combination with acetic acid was identified as a powerful catalyst for the condensation of oxindole with aldehydes, acetone or cyclic ketones. A variety of 3-alkyloxindoles could be readily prepared in 10 mmol scale via the sequential benzylamine acetate catalyzed condensation of oxindoles with aldehydes (or ketones) and conjugate reduction by NaBH4.