165532-43-4

Basic information

• Product Name: ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate
• Synonyms: ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate
• CAS NO: 165532-43-4
• Molecular Weight: 235.24
• Mol File: 165532-43-4.mol

Chemical Properties

• CAS DataBase Reference: ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate(165532-43-4)
• EPA Substance Registry System: ethyl 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylate(165532-43-4)

Safety Data

• Hazardous Substances Data: 165532-43-4(Hazardous Substances Data)

Upstream product

• 119841-74-6 N,2-dihydroxybenzenecarbonimidoyl chloride 
• 140-88-5 ethyl acrylate 
• 90-02-8 salicylaldehyde 
• 94-67-7 salicylaldehyde-oxime 

Downstream Products

• 1235471-24-5 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid 4-(sec-butyl)phenylamide 
• 712347-85-8 4,5-dihydro-3-(2-hydroxyphenyl)isoxazole-5-carboxylic acid 

Relevant articles and documents

[2 + 2 + 1] Cycloaddition ofN-tosylhydrazones,tert-butyl nitrite and alkenes: a general and practical access to isoxazolines

N-Tosylhydrazones have proven to be versatile synthons over the past several decades. However, to our knowledge, the construction of isoxazolines based onN-tosylhydrazones has not been examined. Herein, we report the first demonstrations of [2 + 2 + 1] cycloaddition reactions that allow the facile synthesis of isoxazolines, employingN-tosylhydrazones,tert-butyl nitrite (TBN) and alkenes as reactants. This process represents a new type of cycloaddition reaction with a distinct mechanism that does not involve the participation of nitrile oxides. This approach is both general and practical and exhibits a wide substrate scope, nearly universal functional group compatibility, tolerance of moisture and air, the potential for functionalization of complex bioactive molecules and is readily scaled up. Both control experiments and theoretical calculations indicate that this transformation proceedsviathein situgeneration of a nitronate from the coupling ofN-tosylhydrazone and TBN, followed by cycloaddition with an alkene and subsequent elimination of atert-butyloxy group to give the desired isoxazoline.

Simple preparation method of isoxazoline

The invention discloses a simple preparation method of isoxazoline. The simple preparation method is characterized in that a series of isoxazoline compounds are efficiently synthesized by using aldehyde, p-toluenesulfonhydrazide, olefin and tert-butyl nit

Synthesis and biological activity of 3-substituted isoxazolecarboxamides

A series of novel 3-substituted isoxazolecarboxamides have been prepared. A key step was 1,3-dipolar cycloaddition of nitrile oxides to α,β-unsaturated esters. Some of these compounds exhibited high fungicidal activities against Alternaria alternata, Botrytis cinerea, Rhizoctonia solani, Fusarium culmorum, and Phytophthora cactorum.