97053-63-9

Basic information

• Product Name: trans-3,5-bis-(methoxycarbonyl)-4-pentadeuteriophenyl-2-isoxazoline-2-oxide
• CAS NO: 97053-63-9
• Molecular Weight: 284.21
• Mol File: 97053-63-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: trans-3,5-bis-(methoxycarbonyl)-4-pentadeuteriophenyl-2-isoxazoline-2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3,5-bis-(methoxycarbonyl)-4-pentadeuteriophenyl-2-isoxazoline-2-oxide(97053-63-9)
• EPA Substance Registry System: trans-3,5-bis-(methoxycarbonyl)-4-pentadeuteriophenyl-2-isoxazoline-2-oxide(97053-63-9)

Safety Data

• Hazardous Substances Data: 97053-63-9(Hazardous Substances Data)

Upstream product

• 2483-57-0 methyl 2-nitroacetate 
• 14132-51-5 2,3,4,5,6-pentadeuteriobenzaldehyde 

Relevant articles and documents

A Novel Ring Transformation of 3,5-Bis(methoxycarbonyl)-4-phenyl-2-isoxazoline-2-oxides into 2-Methoxycarbonyl-1-oxido-3H-indole-3-acetates

3,5-Bis(methoxycarbonyl)-4-phenyl-2-isoxazoline-2-oxides (1) were readily transformed into 2-methoxycarbonyl-1-oxido-3H-indole-3-acetates (2) in the presence of Lewis acids such as titanium tetrachloride in dichloromethane.The reaction may occur via initial N-O bond fission to form an ionic intermediate (B), which cyclizes to 3H-indole-1-oxide (2) through an intramolecular aromatic substitution, on the basis of deuterium incorporation experiments as well as stereochemical considerations.With regard to the substituent effect, the reaction of meta-substituted phenylisoxazolines (1f-h) having an o,p-orientating group such as halogen was facilitated to provide 5-substituted 3H-indole-1-oxides (2f-h) in good yield.In contrast, the reaction of para-substituted compounds (1b-e) having the same substituents gave benzofuro-isoxazoles(7b-e) preferentially, rather than 6-substituted 3H-indole-1-oxides (2b-e). Keywords -- 2-isoxazoline-2-oxide; 1-oxido-3H-indole-3-acetate; titanium tetrachloride; ring transformation; intramolecular aromatic substitution