217446-37-2

Basic information

• Product Name: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(2-methylpropyl)-
• CAS NO: 217446-37-2
• Molecular Formula: C14H17NO3
• Molecular Weight: 247.294
• Mol File: 217446-37-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(2-methylpropyl)-(217446-37-2)
• EPA Substance Registry System: 5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(2-methylpropyl)-(217446-37-2)

Safety Data

• Hazardous Substances Data: 217446-37-2(Hazardous Substances Data)

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 328-39-2 LEUCINE 
• 6322-53-8 leucine methyl ester hydrochloride 

Downstream Products

• 1037516-58-7 (S)-methyl 2-(4-methoxybenzamido)-4-methylpentanoate 
• 1379691-04-9 4-iso-butyl-2-(4-methoxyphenyl)oxazol-5-yl (4-methoxyphenyl) carbonate 
• 1060771-63-2 2-(4-methoxyphenyl)-4-isobutyloxazol-5-yl 1,1,1-trichloro-2-methylpropan-2-yl carbonate 
• 1017848-85-9 phenyl 4-iso-butyl-2-(4-methoxyphenyl)-5-oxo-4,5-dihydrooxazole-4-carboxylate 
• 217446-12-3 benzyl (4-isobutyl-2-(4-methoxyphenyl)oxazol-5-yl) carbonate 
• 627877-66-1 4-iso-butyl-2-(4-methoxyphenyl)oxazol-5-yl phenyl carbonate 

Relevant articles and documents

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.

Tandem multi-step synthesis of C-carboxyazlactones promoted by N-heterocyclic carbenes

Cascade reaction sequences incorporating N-heterocyclic carbene-based organocatalysis have been developed that allow the direct preparation of a range of (±)-4-phenoxycarbonylazlactones in good isolated yields (66-84%) from the corresponding N-p-anisoyl amino acids. The Royal Society of Chemistry.