244250-31-5

Basic information

• Product Name: 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline
• Synonyms: 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline
• CAS NO: 244250-31-5
• Molecular Weight: 783.448
• Mol File: 244250-31-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline(244250-31-5)
• EPA Substance Registry System: 5,8-dibromo-1-(3,4-dimethoxyphenacyl)-1,2-dihydro-6,7-dimethoxy-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinoline(244250-31-5)

Safety Data

• Hazardous Substances Data: 244250-31-5(Hazardous Substances Data)

Upstream product

• 79631-01-9 1,2-dimethoxy-4-<1-<(1,1-dimethylethyl)dimethylsilyloxy>ethenyl>benzene 
• 244250-25-7 5,8-dibromo-6,7-dimethoxyisoquinoline 
• 244250-20-2 N-(p-nitrophenyl)sulfonyl-L-alanyl chloride 
• 59724-75-3 N-(p-nitrophenylsulfonyl)-(S)-alanine 
• 15248-39-2 6,7-dimethoxyisoquinoline 

Downstream Products

• 399559-47-8 2-[N-(p-aminophenyl)sulfonyl-(S)-alanyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-1-(3,4-dimethoxyphenethyl)isoquinoline 
• 123355-84-0 (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 130010-32-1 (R)-1-(3',4'-dimethoxyphenethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries

5,8-Dibromoisoquinoline derivatives were allowed to react with a nucleophile (silyl enol ether or allyltributyltin) in the presence of an acyl chloride derived from (S)-alanine to afford the 1,2-addition products in good chemical yields and high stereoselectivity. The bromo groups were readily removed by a reduction process in which the double bond at C3-C4 was also reduced. Thus the reaction system provided a general method to synthesize asymmetric 1-substituted tetrahydroisoquinolines. In order to determine the absolute configuration of the reaction product, (-)-homolaudanosine was synthesized in an enantiopure form. The stereoselectivity was rationally understood from the conformation of intermediary N-acylated isoquinolinium salts.