58144-67-5

Basic information

• Product Name: Methanone, (4-chlorophenyl)(5-phenyl-3-isoxazolyl)-
• CAS NO: 58144-67-5
• Molecular Formula: C16H10ClNO2
• Molecular Weight: 283.714
• Mol File: 58144-67-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methanone, (4-chlorophenyl)(5-phenyl-3-isoxazolyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (4-chlorophenyl)(5-phenyl-3-isoxazolyl)-(58144-67-5)
• EPA Substance Registry System: Methanone, (4-chlorophenyl)(5-phenyl-3-isoxazolyl)-(58144-67-5)

Safety Data

• Hazardous Substances Data: 58144-67-5(Hazardous Substances Data)

Upstream product

• 99-91-2 para-chloroacetophenone 
• 536-74-3 phenylacetylene 
• 1638618-21-9 4-(4-chlorophenyl)-1-phenylbut-3-yn-1-ol 
• 5468-33-7 1-(4-chlorophenyl)-2-nitroethan-1-one 
• 6305-05-1 2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 

Relevant articles and documents

Synthesis of 3-Acyl-Isoxazoles via Radical 5-endo trig Cyclization of β,γ-Unsaturated Ketones with NaNO2

Here we report a facile cyclization reaction of β,γ-unsaturated ketones with NaNO2 under mild conditions to construct 3-acyl-isoxazoles. This transformation is realized via nitrosation of the activated methylene, radical 5-endo trig cyclization

Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

Synthesis of tetrafunctionalized 2-azido-3-hydroxy-1,4-diones and their transformation into 5-substituted 3-acylisoxazoles

An efficient synthesis of 2-azido-3-hydroxy-1,4-diones, based on the base-induced coupling of α-azido ketones and α-oxo aldehydes, has been developed. The coupling reaction took place with moderate to good diastereoselectivity. The relative configurations of the adducts have been determined by X-ray analysis. Treatment of tetrafunctionalized synthons 2-azido-3-hydroxy-1,4-diones with mesyl chloride in the presence of base afforded 5-substituted 3-acylisoxazoles, through 2-azido-2-alkene-1,4-dione intermediates. Analogous treatment of α-azido ketones with α-oxo esters resulted in the formation of the unstable 3-azido-2-hydroxy-4-oxobut-anoates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.