108817-72-7

Basic information

• Product Name: 4-Isoxazolecarboxylic acid, 2,3-dihydro-2,5-dimethyl-3-phenyl-, methyl ester
• Synonyms: 2,5-Dimethyl-3-phenyl-2,3-dihydro-isoxazole-4-carboxylic acid methyl ester;2,5-dimethyl-3-phenyl-4-carbomethoxyisoxazolidine
• CAS NO: 108817-72-7
• Molecular Formula: C13H15NO3
• Molecular Weight: 233.26300
• Mol File: 108817-72-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Isoxazolecarboxylic acid, 2,3-dihydro-2,5-dimethyl-3-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isoxazolecarboxylic acid, 2,3-dihydro-2,5-dimethyl-3-phenyl-, methyl ester(108817-72-7)
• EPA Substance Registry System: 4-Isoxazolecarboxylic acid, 2,3-dihydro-2,5-dimethyl-3-phenyl-, methyl ester(108817-72-7)

Safety Data

• Hazardous Substances Data: 108817-72-7(Hazardous Substances Data)

Upstream product

• 1233235-02-3 2,5-dimethyl-3-phenyl-2,3-dihydroisoxazole-4-carboxylic acid 
• 74-88-4 methyl iodide 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 55370-56-4 3-Morpholinocrotonsaeure-methylester 
• 7166-18-9 methyl β-chlorocrotonate 
• 108817-71-6 2-methyl-5-methylene-3-phenyl-4-carbomethoxyisoxazolidine 
• 110601-13-3 2-Methyl-5-methylene-3-phenyl-isoxazolidine-4-carboxylic acid methyl ester 
• 18913-35-4 methyl buta-2,3-dienoate 
• 3376-23-6 C-phenyl-N-methylnitrone 

Downstream Products

• 20048-06-0 (E)-2-acetyl-1-phenyl-prop-1,2-enoic acid methyl ester 

Relevant articles and documents

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

A STUDY OF THE 5-EXO METHYLENE-ISOXAZOLIDINE TO 3-PYRROLIDINONE REARRANGEMENT

Dipolar cycloaddition of nitrones with carbomethoxy susbstituted allenes gives 5-exo methylene substituted isoxazolidines which rearrange upon thermolysis to 3-pyrrolidinones.