372965-71-4

Basic information

• Product Name: (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine
• Synonyms: (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine
• CAS NO: 372965-71-4
• Molecular Weight: 366.503
• Mol File: 372965-71-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine(372965-71-4)
• EPA Substance Registry System: (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine(372965-71-4)

Safety Data

• Hazardous Substances Data: 372965-71-4(Hazardous Substances Data)

Upstream product

• 372965-65-6 (S)-N-benzyl-N-(4-methylpent-3-enyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester 
• 372965-66-7 (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol 
• 372965-67-8 (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninal 
• 372965-64-5 (S)-N-(4-methylpent-3-enyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester 
• 104528-83-8 (S)-(+)-3,4-dimethoxyphenylalanine ethyl ester 
• 32161-30-1 (S)-3,4-dimethoxyphenylalanine 
• 372965-69-0 (1S,4aS,10aS)-2-benzyl-7-chloro-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine 

Relevant articles and documents

Pictet-Spengler cyclization vs. Aminal formation: Competing reaction pathways of benzo[b][1,7]naphthyridines controlled by the configuration

Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-a-amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular animal formation.