Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-, (2R)-

Base Information

• Chemical Name: Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-, (2R)-
• CAS No.: 608525-25-3
• Molecular Formula: C19H23NO2
• Molecular Weight: 297.397
• Mol file: 608525-25-3.mol

Synonyms:

Chemical Property of Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-, (2R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-, (2R)-

There total 7 articles about Quinoline, 2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydro-, (2R)- 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%

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline (95279-34-8) → (R)-2-(3’,4’-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline (608525-25-3)

Guidance literature:

With C₃₄H₃₉F₃N₂O₅RuS₂; hydrogen; In methanol; at 25 ℃; for 14h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja2023042

Reference yield:

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline (95279-34-8) → (R)-2-(3’,4’-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline (608525-25-3) + (-)-(2S)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline (608525-32-2)

Guidance literature:

With hydrogen; iodine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-G₂DenBINAP; In tetrahydrofuran; at 20 ℃; for 1.5h; under 34202.3 Torr; Title compound not separated from byproducts.;

DOI:10.1021/ol0631410

Reference yield:

2-(3,4-dimethoxy-β-phenethyl)-1,2,3,4-tetrahydroquinoline (104967-54-6) → (R)-2-(3’,4’-dimethoxyphenethyl)-1,2,3,4-tetrahydroquinoline (608525-25-3)

Guidance literature:

With borane-ammonia complex; In aq. phosphate buffer; at 30 ℃; for 96h; pH=7.4; Enzymatic reaction;

DOI:10.1021/acscatal.8b01220

upstream raw materials:

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-quinoline

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

2-methylquinoline

4-bromomethyl-1,2-dimethoxybenzene

Downstream raw materials:

(R)-2-[2-(3,4-dimethoxyphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydroquinoline

Refernces

• 1、 Cosgrove, Sebastian C.,Hussain, Shahed,Turner, Nicholas J.,Marsden, Stephen P.. "Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines". . p. 5570 - 5573. Retrieved 2018/05/25.
• 2、 Ding, Zi-Yuan,Wang, Tianli,He, Yan-Mei,Chen, Fei,Zhou, Hai-Feng,Fan, Qing-Hua,Guo, Qingxiang,Chan, Albert S. C.. "Highly enantioselective synthesis of chiral tetrahydroquinolines and tetrahydroisoquinolines by ruthenium-catalyzed asymmetric hydrogenation in ionic liquid". supporting information. p. 3727 - 3735. Retrieved 2014/01/06.