1239897-00-7

Basic information

• Product Name: (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline
• Synonyms: (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline
• CAS NO: 1239897-00-7
• Molecular Weight: 424.499
• Mol File: 1239897-00-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline(1239897-00-7)
• EPA Substance Registry System: (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline(1239897-00-7)

Safety Data

• Hazardous Substances Data: 1239897-00-7(Hazardous Substances Data)

Upstream product

• 91-63-4 2-methylquinoline 
• 85-44-9 phthalic anhydride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 1780-19-4 (R)-1,2,3,4-tetrahydroquinaldine 

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.

Synthesis of enantiomers of 6-nitro-and 6-amino-2-methyl-1,2,3,4- tetrahydroquinolines

Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the di

Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides

A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent.