1239896-97-9

Basic information

• Product Name: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline
• Synonyms: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline
• CAS NO: 1239896-97-9
• Molecular Weight: 426.472
• Mol File: 1239896-97-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline(1239896-97-9)
• EPA Substance Registry System: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline(1239896-97-9)

Safety Data

• Hazardous Substances Data: 1239896-97-9(Hazardous Substances Data)

Upstream product

• 32329-20-7 (RS)-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 

Relevant articles and documents

A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines

The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4- tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee >99%) was developed.

Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides

The acylative kinetic resolution of racemic 2-methyl-1,2,3,4- tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)- alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe > H > NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution.