(4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one

Base Information

• Chemical Name: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one
• CAS No.: 866394-49-2
• Molecular Formula: C₁₇H₂₀O₃
• Molecular Weight: 272.344
• Mol file: 866394-49-2.mol

Synonyms:(R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one

Chemical Property of (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one

Chemical Property:

• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

(4R)-4-(3,4-Dimethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (4R)-4-(3,4-Dimethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one is an intermediate in the synthesis of Mesembrine (M338950), a serotonin-uptake inhibitor which occurs naturally as the (-)-form.

Technology Process of (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one

There total 9 articles about (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one 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: 92.0%

(7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol (866394-48-1) → (R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one (866394-49-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water;

DOI:10.1021/jo0511039

Reference yield: 82.0%

(-)-(S)-2-allyl-2-(3,4-dimethoxyphenyl)-5-oxohexanal → (R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one (866394-49-2)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1.5h; Heating;

DOI:10.1021/jo701833v

Reference yield: 70.0%

(S)-6-allyl-3-ethoxy-6-(3',4'-dimethoxy-phenyl)cyclohex-2-en-1-one → (R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one (866394-49-2)

Guidance literature:

(S)-6-allyl-3-ethoxy-6-(3',4'-dimethoxy-phenyl)cyclohex-2-en-1-one; With diisobutylaluminium hydride; In toluene; at -78 - -20 ℃; for 2.33333h; Inert atmosphere;

With hydrogenchloride; In methanol; water; at -78 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04125

upstream raw materials:

(7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol

cyclohexanedione monoethylene ketal

4-Bromoveratrole

4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene

Downstream raw materials:

(-)-mesembrine

(R)-4-(3,4-Dimethoxy-phenyl)-4-(2-methylamino-ethyl)-cyclohex-2-enol

Toluene-4-sulfonic acid 2-[(R)-1-(3,4-dimethoxy-phenyl)-4-hydroxy-cyclohex-2-enyl]-ethyl ester

(4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole

Refernces

• 1、 Wang, Wei,Dai, Jun,Yang, Qiqiong,Deng, Yu-Hua,Peng, Fangzhi,Shao, Zhihui. "Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine". . p. 920 - 924. Retrieved 2021/02/16.