1,2,3,4-Tetrahydro-2-(3,4-dimethoxyphenethyl)-1-methylquinoline

Base Information

• Chemical Name: 1,2,3,4-Tetrahydro-2-(3,4-dimethoxyphenethyl)-1-methylquinoline
• CAS No.: 442-33-1
• Molecular Formula: C20H25NO2
• Molecular Weight: 311.41800
• Mol file: 442-33-1.mol

Synonyms:

Chemical Property of 1,2,3,4-Tetrahydro-2-(3,4-dimethoxyphenethyl)-1-methylquinoline

Chemical Property:

• Vapor Pressure: 2.84E-08mmHg at 25°C
• Melting Point: 56°
• PSA: 21.70000
• LogP: 4.15260

Purity/Quality:

CUSPAREINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3,4-Tetrahydro-2-(3,4-dimethoxyphenethyl)-1-methylquinoline

There total 87 articles about 1,2,3,4-Tetrahydro-2-(3,4-dimethoxyphenethyl)-1-methylquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-methyl-2-(3,4-dimethoxyphenylethynyl)-1,2,3,4-tetrahydroquinoline → 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinolineanol (104967-55-7,442-33-1)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃;

Reference yield: 98.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline (608525-32-2) → (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline (442-33-1)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In water; acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.03.037

Reference yield: 95.0%

2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline (104967-54-6) + methyl iodide (74-88-4) → 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinolineanol (104967-55-7,442-33-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; for 20h; Reflux;

DOI:10.1039/c9ob02673h

upstream raw materials:

2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline

methyl iodide

2-(3,4-dimethoxyphenylethenyl)quinoline

(E)-1-bromo-2-(3,4-dimethoxyphenyl)ethene

Refernces

• 1、 Rueping, Magnus,Antonchick, Andrey P.,Theissmann, Thomas. "A highly enantioselective Bronsted acid catalyzed cascade reaction: Organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids". . p. 3683 - 3686. Retrieved 2006.
• 2、 Berthold, Dino,Breit, Bernhard. "Asymmetric total syntheses of (-)-Angustureine and (-)-cuspareine via rhodium-catalyzed hydroamination". . p. 565 - 568. Retrieved 2020.
• 3、 Maestro, Aitor,Lemaire, Sebastien,Harutyunyan, Syuzanna R.. "Cu(I)-Catalyzed Alkynylation of Quinolones". supporting information. p. 1228 - 1231. Retrieved 2022/02/14.
• 4、 Thorve, Pradip Ramdas,Maji, Biplab. "Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst". supporting information. p. 542 - 547. Retrieved 2021/01/26.