6392-40-1

Basic information

• Product Name: 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol
• CAS NO: 6392-40-1
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.3642
• Mol File: 6392-40-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 472.1°C at 760 mmHg
• Flash Point: 239.3°C
• Density: 1.164g/cm³
• Vapor Pressure: 1.55E-09mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol(6392-40-1)
• EPA Substance Registry System: 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol(6392-40-1)

Safety Data

• Hazardous Substances Data: 6392-40-1(Hazardous Substances Data)

Upstream product

• 10214-84-3 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-hydroxyphenyl)acetamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 156-38-7 4-hydroxyphenylacetate 
• 123285-94-9 (3R,10bS)-8,9-dimethoxy-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo<2.3-a>isoquinoline 
• 655245-11-7 1-(4-benzyloxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1609169-60-9 tert-butyl 1-(4-hydroxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1609169-59-6 tert-butyl 1-(4-(benzyloxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 47626-99-3 1-(4-(benzyloxy)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 5884-31-1 2-(4-benzyloxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide 
• 611182-78-6 [4-(bromomethyl)phenoxy][tri(propan-2-yl)]silane 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 1344118-35-9 1-[4-(triisopropylsilyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1356165-28-0 1-[4-(triisopropylsilyloxy)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 913985-87-2 8',9'-dimethoxy-1',5',6',10b'-tetrahydro-4H-spiro(cyclohexa-2,5-diene-1,2'-pyrrolo[2,1-a]isoquinoline)-3',4-dione 

Downstream Products

• 5701-00-8 (R)-O-methylarmepavine 

Relevant articles and documents

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet-Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

We present a systematic investigation on an improved variant of the N-acyl-Pictet-Spengler condensation for the synthesis of 1-benzyltetrahydroisoquinolines, based on our recently published synthesis of N-methylcoclaurine, exemplified by the total syntheses of 10 alkaloids in racemic form. Major advantages are a) using ω-methoxystyrenes as convenient alternatives to arylacetaldehydes, and b) using the ethoxycarbonyl residue for both activating the arylethylamine precursors for the cyclization reaction, and, as a significant extension, also as protective group for phenolic residues. After ring closure, the ethoxycarbonyl-protected phenols are deprotected simultaneously with the further processing of the carbamate group, either following route A (lithium alanate reduction) to give N-methylated phenolic products, or following route B (treatment with excess methyllithium) to give the corresponding alkaloids with free N-H function. This dual use of the ethoxycarbonyl group shortens the synthetic routes to hydroxylated 1-benzyltetrahydroisoquinolines significantly. Not surprisingly, these ten alkaloids did not show noteworthy effects on TPC2 cation channels and the tumor cell line VCR-R CEM, and did not exhibit P-glycoprotein blocking activity. But due to their free phenolic groups they can serve as valuable intermediates for novel derivatives addressing all of these targets, based on previous evidence for structure-activity relationships in this chemotype.

Total Synthesis of (S, S)-Tetramethylmagnolamine via Aerobic Desymmetrization

We describe a concise synthesis of the pseudodimeric tetrahydroisoqunoline alkaloid (S,S)-tetramethylmagnolamine by a catalytic aerobic desymmetrization of phenols. Desymmetrization reactions increase molecular complexity with high levels of efficiency, b

Design, synthesis and biological evaluation of benzylisoquinoline derivatives as multifunctional agents against Alzheimer's disease

A novel series of benzylisoquinoline derivatives were designed, synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). The screening results showed that most of the compounds significantly inhibited cholinesterases (ChEs),