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

Uses

3,4-Dihydropapaverine is an impurity of Papaverine (P190500), smooth muscle relaxant found in opium. Vasodilator (cerebral).

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

• 27160-08-3 2-(3,4-dimethoxyphenyl)-ethylchloride 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 796074-04-9 (2,3-dimethoxy-phenyl)-acetic acid-(2,3-dimethoxy-phenethylamide) 
• 13074-31-2 Tetrahydropapaverine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 91-16-7 1,2-dimethoxybenzene 
• 13230-71-2 N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 7417-21-2 2-(3,4-dimethoxyphenyl)ethyl alcohol 
• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 
• 50896-90-7 (-) N-norlaudanosine 
• 14773-41-2 3-(3,4-dimethoxyphenyl)propionic acid amide 
• 6831-56-7 2',3'-dimethoxyphenylacetyl chloride 

Downstream Products

• 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 
• 4747-98-2 S-(-)-Norlaudanosine 
• 50896-90-7 (-) N-norlaudanosine 
• 54417-52-6 (S)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3.4-tetrahydroisoquinoline hydrochloride 
• 54417-53-7 (R)-tetrahydropapaverine hydrochloride 
• 20345-69-1 3,4-dihydropapaveraldine 
• 6429-04-5 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride 

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.