31151-40-3

Basic information

• Product Name: Ethanone, 1-cyclohexyl-2-diazo-
• CAS NO: 31151-40-3
• Molecular Formula: C8H12N2O
• Molecular Weight: 152.196
• Mol File: 31151-40-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-cyclohexyl-2-diazo-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-cyclohexyl-2-diazo-(31151-40-3)
• EPA Substance Registry System: Ethanone, 1-cyclohexyl-2-diazo-(31151-40-3)

Safety Data

• Hazardous Substances Data: 31151-40-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 10500-30-8 cyclohexanoyl bromide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1315549-98-4 1-cyclohexyl-2-(trifluoromethanesulfonyl)ethanone 
• 851460-95-2 dithiocarbonic acid S-(2-cyclohexyl-2-oxoethyl) ester O-ethyl ester 
• 1426319-00-7 ethyl (2R,3S)-2-(4-chlorophenylamino)-4-cyclohexyl-3-hydroxy-4-oxobutanoate 
• 1203707-86-1 1-cyclohexyl-3,4-dihydroxybutane-1,2-dione 
• 1203708-03-5 1-cyclohexyl-2-diazo-3,4-dihydroxybutan-1-one 
• 4354-49-8 2-cyclohexyl-2-oxoethanoic acid 
• 6007-97-2 2-cyclohexyl-2-methoxy-oxirane 

Relevant articles and documents

α-Xanthylmethyl Ketones from α-Diazo ketones

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p -toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.

Dihydrofurans from α-diazoketones due to facile ring opening - Cyclization of donor-acceptor cyclopropane intermediates

A series of α-diazoketones, 8, 25, 28, 31, and 34, have been synthesized and their reaction with ethyl vinyl ether examined under various reaction conditions. In the presence of metal salts (Rh2(OAc)4, Pd(OAc)2, CuCl) the ethoxydihydrofurans 12, 37, 39, 41, and 43 are produced. Sensitized irradiation of the α-diazoketone 8 afforded the dihydrofuran 12 plus cyclobutanone 7, while direct photolysis of α-diazoketones 8, 25, 28, 31, and 34 gave the cyclobutanones 7, 38, 40, 42, and 44, respectively. A sample of the cyclopropylketone 45 was isolated from the rhodium(II) acetate mediated reaction of 34 and its facile rearrangement to dihydrofuran 43 demonstrated. Collectively, these results indicate that the initial product from the reaction of an α-diazoketone with an electron-rich alkene such as ethyl vinyl ether is a cyclopropylketone. The donnor-acceptor substitution pattern of this intermediate results in spontaneous rearrangement to a dihydrofuran. Thus a direct dipolar cycloaddition mechanism is not involved when α-diazoketones react with enol ethers under metal-mediated conditions. Instead, these reactions follow a cyclopropanation rearrangement or, more accurately, cyclopropanation - ring opening - cyclization pathway.

Oxidation of diazo compounds by dimethyl dioxirane: An extremely mild and efficient method for the preparation of labile α-oxo-aldehydes

A novel method for the preparation of α-oxo-aldehydes by dimethyl dioxirane oxidation of α-diazoketones is described. The procedure is particularly useful when the desired compound cannot be purified by chromatography or distillation: the by-products (ace