139334-35-3

Basic information

• Product Name: 4-Oxazolecarboxylic acid, 4,5-dihydro-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-, methyl ester, cis-
• CAS NO: 139334-35-3
• Molecular Formula: C18H16N2O6
• Molecular Weight: 356.335
• Mol File: 139334-35-3.mol

Chemical Properties

• CAS DataBase Reference: 4-Oxazolecarboxylic acid, 4,5-dihydro-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-, methyl ester, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolecarboxylic acid, 4,5-dihydro-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-, methyl ester, cis-(139334-35-3)
• EPA Substance Registry System: 4-Oxazolecarboxylic acid, 4,5-dihydro-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-, methyl ester, cis-(139334-35-3)

Safety Data

• Hazardous Substances Data: 139334-35-3(Hazardous Substances Data)

Upstream product

• 67567-57-1 2-(p-methoxyphenyl)-5-methoxyoxazole 
• 555-16-8 4-nitrobenzaldehdye 

Relevant articles and documents

Stereoselective synthesis of 2-oxazoline-4-carboxylates through lewis acid-catalyzed formal [3 + 2] cycloadditions of 5-alkoxyoxazoles with aldehydes: Catalytic effect of methylaluminum β-binaphthoxide on cis- selectivity

The formal [3 + 2] cycloadditions of 5-methoxy-2-(p-methoxyphenyl) oxazole with benzaldehyde, para- and meta-substituted benzaldehydes, propanal, cinnamaldehyde, and heterocyclic carboxaldehydes in the presence of methylaluminum β-binaphthoxide gave the corresponding methyl 5-alkyl-2-(p- methoxyphenyl)-2-oxazoline-4-carboxylates with high cis-selectivity (up to 98%). The use of ortho-substituted benzaldehydes resulted in a decrease in the cis-selectivity. The reaction of 5-methoxy-2-(p-methoxyphenyl)oxazole with benzaldehyde in the presence of titanium(IV) chloride or tin(IV) chloride gave the corresponding trans-2-oxazoline-4-carboxylate with 85-86% trans-selectivity. The reaction of ethyl glyoxylate with 5-ethoxy-2- phenyloxazole catalyzed by a 1:1 mixture of titanium(IV) chloride and titanium tetraisopropoxide gave diethyl 2-phenyl-2-oxazoline-4,5- dicarboxylate with a preference for cis-selectivity (cis/trans = 84:6). The cis-selectivity of the reaction in the presence of methylaluminum β- binaphthoxide can be explained by an antiperiplanar approach of the C4-C5 double bond of the oxazole to the aldehyde coordinated to the catalyst, followed by ring opening of the oxazole through a stepwise pathway involving zwitterionic intermediates.

Enantioselective synthesis of cis-2-oxazoline-4-carboxylates by Lewis acid catalyzed formal [3+2] cycloadditions of 5-alkoxyoxazoles with aldehydes

Formal [3+2] cycloaddition of 2-o-methoxyphenyl-5-methoxyoxazole with benzaldehyde, m- and p-substituted benzaldehydes in the presence of 30 mol% of (R)-methylaluminum β-binaphthoxide, which was prepared from (R)-2,2'-dihydroxy-1,1'-dinaphthyl and 1.1 - 1.05 equiv. of trimethylaluminum, gave cis-2-oxazoline-4-carboxylates in high enantoselectivity.

Reactions of 5-alkoxyoxazoles with aldehydes in the presence of Lewis acid: Regio- and stereoselective formation of 4-alkoxycarbonyl-2-oxazolines

The [3 + 2] cycloaddition of 5-alkoxyoxazoles with aldehydes in the presence of the organoaluminum reagent, which was prepared from (±)-2,2′-dihydroxy-1,1′-dinaphthyl and AlMe3, gave cis-4-alkoxycarbonyl-2-oxazolines in high regio- and stereoselective manner.