10268-39-0

Basic information

• Product Name: 6,7-dimethoxy-1-(4-nitrobenzyl)-3,4-dihydroisoquinoline
• CAS NO: 10268-39-0
• Molecular Formula: C₁₈H₁₈N₂O₄
• Molecular Weight: 326.3465
• Mol File: 10268-39-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 505.1°C at 760 mmHg
• Flash Point: 259.2°C
• Density: 1.26g/cm³
• Vapor Pressure: 7.91E-10mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 6,7-dimethoxy-1-(4-nitrobenzyl)-3,4-dihydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-1-(4-nitrobenzyl)-3,4-dihydroisoquinoline(10268-39-0)
• EPA Substance Registry System: 6,7-dimethoxy-1-(4-nitrobenzyl)-3,4-dihydroisoquinoline(10268-39-0)

Safety Data

• Hazardous Substances Data: 10268-39-0(Hazardous Substances Data)

Upstream product

• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 104-03-0 4-nitrobenzeneacetic acid 
• 10403-40-4 N-(3,4-dimethoxyphenethyl)-4-nitrophenylacetamide 

Downstream Products

• 99-99-0 1-methyl-4-nitrobenzene 
• 1286209-57-1 C₁₈H₁₄N₂O₅ 
• 180623-61-4 3,5-diiodobenzyl-4'-acetamido-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 180623-60-3 1-(4-Acetamido-3,5-diiodobenzyl)-6,7-dimethoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-75-0 1-(4-Acetamido-3-iodobenzyl)-6,7-dimethoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-50-1 6,7-Dimethoxy-1-(4-nitrobenzyl)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-57-8 1-(4-Amino-3,5-diiodobenzyl)-2-trifluoroacetyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 180623-68-1 1-(3,4,5-Triiodobenzyl)-6,7-dimethoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-67-0 1-(3,5-Diiodobenzyl)-6,7-dimethoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-55-6 1-(4-amino-3-iodobenzyl)-2-trifluoroacetyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 180623-53-4 1-(4-Aminobenzyl)-6,7-dimethoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 
• 180623-76-1 1-(4-Acetamido-3-iodobenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 180623-71-6 1-(4-Amino-3,5-diiodobenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 180623-70-5 6,7-Dimethoxy-1-(3,4,5-triiodobenzyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

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.

Oxidation of 1-benzyldihydroisoquinolines or 1- benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines

An environmental-benign methodology to synthesize 1-benzoylisoquinolines from 1-benzyl-3, 4-dihydroisoquinolines or 1-benzyl-1,2,3,4- tetrahydroisoquinolines using dioxygen as an oxidant was developed. This methodology in combination with Bischler-Napieralski reaction leads to a facile synthesis of 1-benzoylisoquinolines from phenylacetic acids and phenylethanamines.

Synthesis of isoquinolines from 2-phenylethylamines, amides, nitriles and carboxylic acids in polyphosphoric acid

A convenient one pot synthesis of 1-, 1.3-substituted 3,4-dihydroisoquinolines 5 enamines 10 and 3-oxo-2,3-dihydroisoquinolines 18 as well as of enamides 22 of isoquinoline from 2-phenyl-, 1,2-diphenylethylamines, phenylacetamides, phenylacetonitriles, N-acylphenylethylamines and carboxylic acids in nonaqueous media has been accomplished.