6957-27-3

Basic information

• Product Name: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline
• Synonyms: 1-[(3,4-dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline;3,4-Dihydropapaverine;Dihydropapaverine;2,4-DIHYDROPAPAVERINE;3,4-Dihydro-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline;1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;3,4-DIHYDROPAPAVERINE(WXG01659);1-(3,4-Dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinoline
• CAS NO: 6957-27-3
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40092
• EINECS: 230-148-3
• Mol File: 6957-27-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 98-99 °C
• Boiling Point: 482.6 °C at 760 mmHg
• Flash Point: 196.9 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 5.28E-09mmHg at 25°C
• PKA: 6.12±0.20(Predicted)
• CAS DataBase Reference: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(6957-27-3)
• EPA Substance Registry System: 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline(6957-27-3)

Safety Data

• Hazardous Substances Data: 6957-27-3(Hazardous Substances Data)

Usage

Description

1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline is a chemical compound derived from the Papaverine family, characterized by its unique structure featuring a 3,4-dihydroisoquinoline core with dimethoxy substitutions at positions 3, 4, 6, and 7, and a 3,4-dimethoxyphenylmethyl group attached to position 1. 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline exhibits properties that make it potentially useful in various applications, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline is used as an impurity in Papaverine, a smooth muscle relaxant and vasodilator found in opium. Its presence in Papaverine may contribute to the overall pharmacological effects of the drug, particularly in its use as a vasodilator for cerebral circulation.
Used in Chemical Research:
As a member of the isoquinoline family, 1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline can be utilized in chemical research for the development of new compounds with potential therapeutic applications. Its unique structure may offer insights into the design of novel drugs targeting specific biological pathways or receptors.
Used in Drug Synthesis:
1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline may also serve as a key intermediate in the synthesis of other pharmaceutically relevant molecules. Its presence in the synthesis process could lead to the development of new drugs with improved efficacy, safety, or pharmacokinetic properties.

InChI:InChI=1/C20H23NO4.BrH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-6,10-12H,7-9H2,1-4H3;1H

Upstream product

• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 13074-31-2 Tetrahydropapaverine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 91-16-7 1,2-dimethoxybenzene 
• 863132-19-8 N-{2-[2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenyl]-ethyl}-2,2,2-trifluoro-acetamide 
• 863132-17-6 (3,4-dimethoxy-phenylethynyl)-trimethyl-silane 
• 14301-36-1 N-[2-(3,4-dimethoxyphenyl)ethyl]formamide 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 863132-09-6 2-[2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenyl]-ethylamine 
• 96625-09-1 {1-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl}-carbamic acid ethyl ester 

Downstream Products

• 104621-38-7 (E)-2-Benzoyl-1-<(3,4-dimethoxyphenyl)methylene>-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1253735-86-2 C₃₃H₃₄BrNO₈ 
• 681431-24-3 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 85544-30-5 (3,4-dimethoxy-phenyl)-(6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-yl)-methanone 
• 58-74-2 Papaverine 
• 522-57-6 papaveraldine 
• 482-76-8 papaverinol 
• 15248-39-2 6,7-dimethoxyisoquinoline 
• 91-16-7 1,2-dimethoxybenzene 
• 61-25-6 papaverine hydrochloride 
• 523-02-4 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline 
• 1344031-84-0 14-(3,4-dimethoxyphenyl)-11,12-dimethoxy-6-(trifluoromethyl)-8,9-dihydro-6H-benzo[7',8']chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinoline 
• 1262209-60-8 14-(3,4-dimethoxyphenyl)-2,11,12-trimethoxy-6-(trifluoromethyl)-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinoline 
• 1262209-61-9 2-bromo-14-(3,4-dimethoxyphenyl)-11,12-dimethoxy-6-(trifluoromethyl)-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinoline 

Relevant articles and documents

COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY

The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

Copper(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to 3,4-dihydroisoquinolines using air (O2) as a clean oxidant

A mild, efficient and eco-friendly method for the oxidation of 1-Bn-DHIQs to 1-Bz-DHIQs without concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs is very important for the syntheses of 1-Bz-DHIQ alkaloids and analogues. In this article, we developed a novel Cu(ii)-catalyzed and acid-promoted highly regioselective oxidation of tautomerizable C(sp3)-H bonds adjacent to the C-1 positions of various 1-Bn-DHIQs. It was observed that when 0.2 equiv. of Cu(OAc)2·2H2O was used as the catalyst, 3.0 equiv. of AcOH was used as the additive and air (O2) was used as a clean oxidant, various 1-Bn-DHIQs could be efficiently oxidized to corresponding 1-Bz-DHIQs at 25 °C in DMSO. Especially, almost no concomitant excessive oxidation of 1-Bz-DHIQs to 1-Bz-IQs was observed during the above reaction. In addition, this method was successfully applied in the first total synthesis of the alkaloid canelillinoxine.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.