76201-90-6

Basic information

• Product Name: 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE
• Synonyms: 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE
• CAS NO: 76201-90-6
• Molecular Formula: C₁₇H₁₆ClNO₂
• Molecular Weight: 301.77
• Mol File: 76201-90-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 418.9°C at 760 mmHg
• Flash Point: 207.2°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 7.67E-07mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE(76201-90-6)
• EPA Substance Registry System: 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE(76201-90-6)

Safety Data

• Hazardous Substances Data: 76201-90-6(Hazardous Substances Data)

Usage

General Description

1-(4-Chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline is a chemical compound that belongs to the isoquinoline family. It has a structure with a 4-chlorophenyl group attached to a dihydroisoquinoline ring with two methoxy groups also attached. 1-(4-CHLOROPHENYL)-6,7-DIMETHOXY-3,4-DIHYDROISOQUINOLINE has potential pharmaceutical applications, as it has been studied for its potential analgesic and anti-inflammatory properties. It is also being investigated for its potential use in the treatment of Parkinson's disease, as it has shown some activity as a dopamine-receptor agonist. Additionally, it has been studied for its potential use in the treatment of drug addiction, as it has shown some activity as a dopamine uptake inhibitor.

InChI:InChI=1/C17H16ClNO2/c1-20-15-9-12-7-8-19-17(14(12)10-16(15)21-2)11-3-5-13(18)6-4-11/h3-6,9-10H,7-8H2,1-2H3

Upstream product

• 98841-62-4 N-(3,4-dimethoxyphenethyl)-4-chlorobenzamide 
• 122-01-0 4-chloro-benzoyl chloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 74-11-3 para-chlorobenzoic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 55507-15-8 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 15994-13-5 N-(4-chlorobenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 243637-11-8 6,7-dimethoxy-1-oxo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 493-49-2 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one 

Downstream Products

• 1448701-62-9 (-)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity

The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.

Mechanistic Studies on Bioinspired Aerobic C-H Oxidation of Amines with an ortho-Quinone Catalyst

We report herein our mechanistic studies of the ortho-quinone-catalyzed aerobic oxidation of primary, secondary, and tertiary amines. Two different catalytic pathways were discovered for the reductive half reactions: for primary amines, the reaction was found to proceed via a transamination pathway, while the reactions with secondary amines and tertiary amines proceeded via hydride transfer. We also found that the amine substrates could significantly promote the regeneration of the ortho-quinone catalyst in the oxidative half reaction, in which a proton transfer occurs between the amine substrates and catechol derivatives (the reduced form of the ortho-quinone catalyst).

One-Pot N-Deprotection and Catalytic Intramolecular Asymmetric Reductive Amination for the Synthesis of Tetrahydroisoquinolines

A one-pot N-Boc deprotection and catalytic intramolecular reductive amination protocol for the preparation of enantiomerically pure tetrahydroisoquinoline alkaloids is described. The iodine-bridged dimeric iridium complexes displayed superb stereoselectivity to give tetrahydroisoquinolines, including several key pharmaceutical drug intermediates, in excellent yields under mild reaction conditions. Three additives played important roles in this reaction: Titanium(IV) isopropoxide and molecular iodine accelerated the transformation of the intermediate imine to the tetrahydroisoquinoline product; p-toluenesulfonic acid contributed to the stereocontrol.