99986-04-6

Basic information

• Product Name: 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline
• Synonyms: 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline
• CAS NO: 99986-04-6
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Mol File: 99986-04-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline(99986-04-6)
• EPA Substance Registry System: 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline(99986-04-6)

Safety Data

• Hazardous Substances Data: 99986-04-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7-dimethoxy-1,2,3,4-tetrahydroquinoline is used as a potential drug candidate for its pharmacological properties, particularly for its effects on the central nervous system. 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline is being studied for its potential use in treating various neurological disorders and conditions, given its interactions with the nervous system.
Used in Research and Development:
In the field of scientific research, 6,7-dimethoxy-1,2,3,4-tetrahydroquinoline serves as a subject of investigation for understanding its mechanisms of action and biological effects. It is utilized in experimental studies to explore its potential as a therapeutic agent and to uncover new avenues for medical applications.

Upstream product

• 91133-47-0 6,7-dimethoxy-3,4-dihydroquinolin-2(1H)-one 
• 873380-59-7 6,7-dimethoxy-3,4-dihydro-1H-quinoline-2-thione 
• 250156-36-6 1-formyl-1,2,3,4-tetrahydro-6,7-dimethoxyquinoline 
• 21164-75-0 3-(4,5-dimethoxy-2-nitro-phenyl)-propionic acid 
• 92042-74-5 3-(4,5-dimethoxy-2-nitro-phenyl)-propionic acid ethyl ester 
• 2107-70-2 3,4-methoxycinnamic acid 
• 250156-20-8 N-(3,4-dimethoxyphenyl)-N-(3-phenylsulfinylpropyl)formamide 
• 250156-30-0 1-formyl-1,2,3,4-tetrahydro-6,7-dimethoxy-4-phenylthioquinoline 
• 1025917-72-9 (3,4-dimethoxy-phenyl)-(3-phenylsulfanyl-propyl)-amine 
• 250156-12-8 N-(3,4-dimethoxyphenyl)-N-(3-phenylthiopropyl)formamide 
• 67278-27-7 6,7-Dimethoxy-chinolin 

Downstream Products

• 858277-76-6 1-(N-acetyl-sulfanilyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-quinoline 
• 67278-27-7 6,7-Dimethoxy-chinolin 
• 1285548-96-0 5-bromo-N-(4-(6,7-dimethoxy-3,4-dihydroquinolin-1(2H)-yl)butyl)-2,3-dimethoxybenzamide 

Relevant articles and documents

Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2, 3-dimethoxy-benzamide (1) is one of the most potent and selective σ2 receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their σ1/σ2 binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher σ1/σ2 selectivity, derived from a higher σ2 affinity and a lower σ1 affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional σ2 receptor binding affinity and selectivity for this active series.

A novel synthesis of 1,2,3,4-tetrahydroquinolines via Pummerer-type reaction of N-aryl-N-[(phenylsulfinyl)propyl]formamide

A synthesis of 1,2,3,4-tetrahydroquinolines (TQs) 13 with two and three methoxyl groups on the benzene ring, was achieved via intramolecular cyclization of N-aryl-N-[(phenylsulfinyl)propyl]formamides 7 utilizing the Pummerer reaction as a key step. The reaction was carried out by using trifluoroacetic anhydride (TFAA) (method A) or TFAA-BF3 · Et2O (method B). The cyclization to 4-PhSTQs 8 proceeded effectively when the reaction center at the benzene ring was electronically activated by a methoxyl group. In the reaction of sulfoxide 7e having two OMe groups in the ortho- and para- positions, a different cyclization reaction leading to 1,5-benzothiazepine derivative 9 was observed, indicating that the high nucleophilicity of the benzene ring caused the unexpected reaction prior to cyclization to 4-PhSTQs 8. This route starting from methoxyanilines provides an efficient and convenient method of TQ synthesis.