1239897-02-9

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: 1239897-02-9
• Molecular Weight: 426.472
• Mol File: 1239897-02-9.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(1239897-02-9)
• EPA Substance Registry System: (2R)-2-methyl-1-[N-phthaloyl-3-cyclohexyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline(1239897-02-9)

Safety Data

• Hazardous Substances Data: 1239897-02-9(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

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.

Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains

A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4] benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee >99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride.