15547-55-4

Basic information

• Product Name: 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• Synonyms: 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE;AKOS BC-3083
• CAS NO: 15547-55-4
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.39
• Mol File: 15547-55-4.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(15547-55-4)
• EPA Substance Registry System: 1-(3,4-DIMETHOXY-PHENYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(15547-55-4)

Safety Data

• Hazardous Substances Data: 15547-55-4(Hazardous Substances Data)

Usage

Uses

1-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is used as a reactant in the preparation of isoquinoline libraries from isoquinolin-1(2H)-ones or via microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reactions.

Upstream product

• 15547-57-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 93-07-2 Veratric acid 
• 33770-41-1 (R)-1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 24456-60-8 6,7-dimethoxy-1-(methylsulfanyl)-3,4-dihydroisoquinoline 
• 24456-59-5 6,7-dimethoxy-3,4-dihydroisoquinoline-1(2H)-thione 
• 18034-37-2 N-<2-(3,4-dimethoxybenzyl)ethyl>-3,4-dimethoxybenzaldimine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 102011-15-4 N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide 
• 142403-96-1 4,4-dimethyl-2-(3,4-dimethoxyphenyl)oxazolidine 
• 128741-53-7 [2-(2-Bromo-4,5-dimethoxy-phenyl)-ethyl]-[1-(3,4-dimethoxy-phenyl)-meth-(E)-ylidene]-amine 

Downstream Products

• 22329-48-2 1-(3,4-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 33770-43-3 (S)-1-1-(3',4'-dimethoxylphenyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 152561-03-0 Acetic acid 1-(3,4-dimethoxy-phenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl ester 
• 879290-24-1 10b-(3,4-dimethoxyphenyl)-8,9-dimethoxy-6,10b-dihydro-5H-isoxazolo[3,2-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester 
• 879290-20-7 1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline N-oxide 
• 15547-57-6 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 

Relevant articles and documents

Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids

A new synthetic route was developed for the preparation of natural products cryptostyline I, II, III and 1-phenyl-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline. The Liebeskind-Srogl palladium-catalyzed carbon-carbon cross-coupling protocol was use

Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method

Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.

Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

Three alkaloids of the cryptostylin series and 20 monomolecular and 3 bimolecular 1-aryltetrahydroisoquinoline derivatives were prepared using the Picte-Spengler reaction.