(+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene

Base Information

• Chemical Name: (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene
• CAS No.: 3569-00-4
• Molecular Formula: C₂₂H₂₆O₄
• Molecular Weight: 354.446
• Mol file: 3569-00-4.mol

Synonyms:

Chemical Property of (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene

There total 35 articles about (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene 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: 85.0%

(1R,2S)-2-Bromomethyl-1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methyl-1,2-dihydro-naphthalene → (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene (3569-00-4,6399-16-2,73366-01-5)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; for 12h; Heating;

DOI:10.1055/s-2001-16086

Reference yield: 71.0%

C30H32O6 → (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene (3569-00-4,6399-16-2,73366-01-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; at 88 ℃; Inert atmosphere;

DOI:10.1246/cl.131179

Reference yield:

(2R,3R)-1,4-Bis-(3,4-dimethoxy-phenyl)-2,3-dimethyl-butane-1,4-diol → (+/-)-trans-4-(3,4-dimethoxyphenyl)-3,4-dihydro-6,7-dimethoxy-2,3-dimethylnaphthalene (3569-00-4,6399-16-2,73366-01-5)

Guidance literature:

(2R,3R)-1,4-Bis-(3,4-dimethoxy-phenyl)-2,3-dimethyl-butane-1,4-diol; With triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

With methanesulfonyl chloride; In dichloromethane; at 0 ℃; for 1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c7ob02848b

upstream raw materials:

all-cis-3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran

nectandrin-B

dimethyl sulfate

bis(3,4-dimethoxyphenyl)methanone

Downstream raw materials:

(±)-isogalbulin

(±)-galbulin

4α-(3,4-dimethoxyphenyl)-2α,3β-dimethyl-6,7-dimethoxy-1-tetralone

Refernces

• 1、 Sakuma, Daichi,Ito, Junki,Sakai, Ryo,Taguchi, Ryota,Nishii, Yoshinori. "Total synthesis of cyclogalgravin and its dicarboxyl analog using sc(otf)3-mediated highly diastereoselective ring expansion of 1-(arylhydroxymethyl)cyclopropanecarboxylates". supporting information. p. 610 - 611. Retrieved 2014/05/20.
• 2、 Yvon,Datta,Le,Charlton. "Synthesis of magnoshinin and cyclogalgravin: Modified stobbe condensation reaction". . p. 1556 - 1560. Retrieved 2007/10/03.