1449213-93-7

Basic information

• Product Name: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine
• Synonyms: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine
• CAS NO: 1449213-93-7
• Molecular Weight: 343.423
• Mol File: 1449213-93-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine(1449213-93-7)
• EPA Substance Registry System: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine(1449213-93-7)

Safety Data

• Hazardous Substances Data: 1449213-93-7(Hazardous Substances Data)

Upstream product

• 1449213-92-6 (E)-4-(4,5-dimethoxy-2-((E)-2-nitrovinyl)styryl)-1,2-dimethoxybenzene 
• 1449213-91-5 (E)-2-(3,4-dimethoxystyryl)-4,5-dimethoxybenzaldehyde 
• 6380-23-0 3,4-dimethoxystyrene 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 

Downstream Products

• 2688-77-9 (S)-laudanosine 
• 85-63-2 (R)-laudanosine 
• 74904-71-5 (E)-2-<2-<2-(3,4-dimethoxyphenyl)ethenyl>-4,5-dimethoxyphenyl>-N-methylethanamine 

Relevant articles and documents

Asymmetric total synthesis of (?)-javaberine A and (?)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine

Asymmetric total synthesis of (?)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide–chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with good enantioselectivity in excellent yield. N-Demethylation of (S)-laudanosine was accomplished by Polonovski-type reaction to give (S)-norlaudanosine. Condensation of (S)-norlaudanosine with homoveratric acid, and subsequent Bischler-Napieralski cyclization, LiAlH4 reduction, and O-demethylation furnished (8R,14S)-(?)-javaberine A, corresponding to antipode of natural javaberine A. (8S,14S)-(?)-Javaberine A, which corresponds to C14-epimer of natural javaberine A, was also successfully synthesized.