217446-35-0

Basic information

• Product Name: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(phenylmethyl)-
• CAS NO: 217446-35-0
• Molecular Formula: C17H15NO3
• Molecular Weight: 281.311
• Mol File: 217446-35-0.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(phenylmethyl)-(217446-35-0)
• EPA Substance Registry System: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(phenylmethyl)-(217446-35-0)

Safety Data

• Hazardous Substances Data: 217446-35-0(Hazardous Substances Data)

Upstream product

• 627877-64-9 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl phenyl carbonate 
• 150-30-1 Phenylalanine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 187836-09-5 methyl (4-methoxybenzoyl)phenylalaninate 
• 103678-74-6 N-(4-methoxybenzoyl)-phenylalanine 

Downstream Products

• 1017848-69-9 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 3,3-dimethylbutan-2-yl carbonate 
• 1017848-54-2 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl (S)-menthyl carbonate 
• 1017848-63-3 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylpropan-2-yl carbonate 
• 1017848-58-6 4-benyl-2-(4-methoxyphenyl)oxazol-5-yl 1-phenylethyl carbonate 
• 217446-10-1 O-benzyloxycarbonyl-2-(4-methoxyphenyl)-4-benzyldihydroazolone 
• 1017848-66-6 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl 3-methylbutan-2-yl carbonate 
• 1072120-74-1 C₃₃H₃₂N₂O₅S 
• 1060771-60-9 4-benzyl-2-(4-methoxyphenyl)oxazol-5-yl (1,1,1-trichloro-2-methylpropan-2-yl) carbonate 
• 1322618-13-2 N-(3-benzyl-2-oxo-4-(phenylamino)chroman-3-yl)-4-methoxybenzamide 
• 1322618-14-3 N-(3-benzyl-2-oxo-4-(phenylamino)chroman-3-yl)-4-methoxybenzamide 
• 1322617-78-6 N-(3-benzyl-4-(2-fluorophenylamino)-2-oxochroman-3-yl)-4-methoxybenzamide 

Relevant articles and documents

Enantioselective synthesis of pyrano[2,3-: C] pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

An enantioselective [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones has been successfully developed through a squaramide catalysis strategy. This protocol provides an efficient and mild access to obtain pyrano[2,3-c]pyrrole scaffolds containing contiguous quaternary and tertiary stereogenic centers in excellent yields (up to 99%) with high levels of diastereo- and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the observed stereoselectivity.

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.