143004-35-7

Basic information

• Product Name: (2R,3R)-3-(4-Nitro-phenyl)-oxirane-2-carboxylic acid methyl ester
• Synonyms: (2R,3R)-3-(4-Nitro-phenyl)-oxirane-2-carboxylic acid methyl ester
• CAS NO: 143004-35-7
• Molecular Weight: 223.185
• Mol File: 143004-35-7.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3R)-3-(4-Nitro-phenyl)-oxirane-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-3-(4-Nitro-phenyl)-oxirane-2-carboxylic acid methyl ester(143004-35-7)
• EPA Substance Registry System: (2R,3R)-3-(4-Nitro-phenyl)-oxirane-2-carboxylic acid methyl ester(143004-35-7)

Safety Data

• Hazardous Substances Data: 143004-35-7(Hazardous Substances Data)

Upstream product

• 142917-83-7 (2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 953-26-4 ethyl 4-nitrocinnamate 
• 555-16-8 4-nitrobenzaldehdye 
• 206346-45-4 (2S,3R)-2-Acetoxy-3-hydroxy-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 19310-31-7 methyl (Z)-3-(4-nitrophenyl)-2-propenoate 
• 67-56-1 methanol 
• 142917-84-8 (2S,3R)-3-Hydroxy-3-(4-nitro-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester 
• 96-34-4 methyl chloroacetate 
• 299179-22-9 3-(4-Nitro-phenyl)-oxirane-2-carbonitrile 

Downstream Products

• 142917-86-0 (1R,2R)-2-Azido-1-(4-nitro-phenyl)-propane-1,3-diol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 56-75-7 chloramphenicol 
• 139618-74-9 Methyl trans-3-(4-nitrophenyl)aziridine-2-carboxylate 
• 244097-09-4 methyl 3-fluoro-3-p-nitrophenylpyruvate 
• 143058-48-4 [(2S,3R)-3-(4-Nitro-phenyl)-oxiranyl]-methanol 
• 50693-98-6 methyl 2-((2-nitrophenyl)thio)acetate 
• 94098-27-8 2-Hydroxy-3-(4-nitro-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 

Relevant articles and documents

Regioselective syntheses of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones from arylglycidates when exposed to 1,2-diaminobenzenes

Representatives of two pharmacologically significant classes of compounds – 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones – obtained in reactions of 1,2-diaminobenzenes with methyl 3-arylglycidates in boiling acetic acid. Substituents in arylglycidates determine the direction of processes. Electron withdrawing substituents (NO2), halogen atoms (Cl, Br, F), as well as the absence of substituents, provide the formation of benzo[b][1,4]diazepin-2(1H)-one derivatives, and electron donating groups (OMe, Me) contribute to the formation of 3-benzylquinoxalin-2(1H)-ones. As a result, a new rare representatives of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones were obtained and a new method for producing 3-benzylquinoxalin-2(1H)-ones has been proposed.

Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver

Several rationally designed analogs of 3-fluoro-2-oxo-3-phenylpropionic acid were chemically synthesized, and the reactions of the hydrate form of these compounds with 4-hydroxyphenylpyruvate dioxygenase from pig liver as inhibitors were examined. Compounds 14a and 14b were found to be potent competitive inhibitors of the enzyme with K(i) values of 10 and 22μM, respectively. Copyright (C) 1999 Elsevier Science Ltd.

Enantioselective Catalytic Epoxidation of Cinnamate Esters

A broad study of the (salen)Mn(III)-catalyzed asymmetric epoxidation of cis-cinnamate esters reveals that the steric properties of the ester group have a profound influence on enantioselectivity in the epoxidation reaction, with bulkier esters affording highest ee's.The sensitivity of the reaction selectivity to the steric properties of the cis-alkene are consistent with a "skewed" side-on approach of olefin to the metal -oxo.The electronic properties of the substrate arene ring substituents do not correlate with epoxidation ee, but instead with the cis/trans partitioning of product formation.Evidence is provided for a non-polar inter mediate in a stepwise oxygen-atom-transfer mechanism.The presence of pyridine N-oxide derivatives has a significant effect on catalysts rates and total turnovers, but negligible influence on the stereoselectivity of epoxidation.A mechanistic basis for the role of these additives is proposed.The synthetic applicability of the cinnamate epoxidation methodology is illustrated in the highly enantioslective synthesis of diltiazem.