20938-53-8

Basic information

• Product Name: 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxy-3-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (+-)-
• Synonyms: dl-1-<3-Methoxy-4-hydroxy-benzyl>-2-methyl-6-methoxy-1,2,3,4-tetrahydro-7-isochinolinol
• CAS NO: 20938-53-8
• Molecular Formula: C19H23NO4
• Molecular Weight: 329.396
• Mol File: 20938-53-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxy-3-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (+-)-(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxy-3-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (+-)-(20938-53-8)
• EPA Substance Registry System: 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxy-3-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (+-)-(20938-53-8)

Safety Data

• Hazardous Substances Data: 20938-53-8(Hazardous Substances Data)

Upstream product

• 71610-35-0 (+/-)-orientaline N-oxide 
• 121-33-5 vanillin 
• 97692-56-3 4-ethoxycarboxy-3-methoxybenzaldehyde 
• 55102-37-9 (+/-)-1,2,3,4-tetrahydro-1-(4'-hydroxy-3'-methoxybenzyl)-6-methoxyisoquinolin-7-ol 
• 138645-11-1 (+/-)-1,2,3,4-tetrahydro-7-hydroxy-1-(4'-hydroxy-3'-methoxybenzyl)-6-methoxyisoquinoline-2-carbaldehyde 
• 96550-48-0 7-Hydroxy-1-(4-hydroxy-3-methoxy-benzyl)-6-methoxy-2-methyl-3,4-dihydro-isoquinolinium 

Downstream Products

• 72142-82-6 1,2-didehydrocoripallinium ion 
• 450-14-6 6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 121-33-5 vanillin 
• 96550-48-0 7-Hydroxy-1-(4-hydroxy-3-methoxy-benzyl)-6-methoxy-2-methyl-3,4-dihydro-isoquinolinium 
• 71610-35-0 (+/-)-orientaline N-oxide 

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.

BIOMIMETIC OXIDATIONS OF BENZYLISOQUINOLINE ALKALOUDS. II. THE BIS(SALICYLALDEHYDE)ETHYLENEDIIMINECOBALT(II)-CATALYZED OXIDATION OF BENZYLISOQUINOLINES WITH OXYGEN

The complex bis(salicylaldehyde)ethylenediiminecobalt(II) (CoII salen) catalyzes the oxidation of benzylisoquinoline alkaloids with oxygen.Aminium radicals are formed and give rise to 1,2-dehydrobenzylisoquinoline ions.Cleavage of the C(1)-C(9) bond via C(9) oxidation is observed in some instances.

Opium alkaloids. XIV: Biosynthesis of aporphines: Detection of orientaline in opium poppy

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