Methyl 3,4-diphenylcyclohex-3-ene-1-carboxylate

Base Information

• Chemical Name: Methyl 3,4-diphenylcyclohex-3-ene-1-carboxylate
• CAS No.: 62543-95-7
• Molecular Formula: C20H20O2
• Molecular Weight: 292.378
• DSSTox Substance ID: DTXSID20506791
• Nikkaji Number: J2.582.539J
• Mol file: 62543-95-7.mol

Synonyms:62543-95-7;SCHEMBL11262331;DTXSID20506791;Methyl 2~3~,2~4~,2~5~,2~6~-tetrahydro[1~1~,2~1~:2~2~,3~1~-terphenyl]-2~4~-carboxylate

Chemical Property of Methyl 3,4-diphenylcyclohex-3-ene-1-carboxylate

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 292.146329876
• Heavy Atom Count: 22
• Complexity: 411

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(=C(C1)C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Methyl 3,4-diphenylcyclohex-3-ene-1-carboxylate

There total 4 articles about Methyl 3,4-diphenylcyclohex-3-ene-1-carboxylate 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: 88.0%

2,3-diphenyl-1,3-butadiene (2548-47-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-4'-carboxylate (62543-95-7)

Guidance literature:

With hydroquinone; at 140 ℃; for 15h;

DOI:10.1246/bcsj.53.3279

Reference yield:

2,3-diphenyl-2,3-butanediol (1636-34-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-4'-carboxylate (62543-95-7)

Guidance literature:

With toluene-4-sulfonic acid; hydroquinone; In acetic anhydride; at 130 - 140 ℃;

Reference yield:

acetophenone p-toluenesulfonylhydrazone (4545-21-5) → methyl 3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-4'-carboxylate (62543-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; lithium tert-butoxide; oxygen; p-benzoquinone / dimethyl sulfoxide / 14 h / 90 °C / 760.05 Torr / Molecular sieve

2: boron trifluoride diethyl etherate / acetonitrile / 24 h / 65 °C

With boron trifluoride diethyl etherate; oxygen; palladium diacetate; p-benzoquinone; lithium tert-butoxide; In dimethyl sulfoxide; acetonitrile; 2: |Diels-Alder Cycloaddition;

DOI:10.1039/c3cc43593h

upstream raw materials:

methanol

3,4-diphenyl-cyclohex-3-enecarboxylic acid

2,3-diphenyl-2,3-butanediol

acrylic acid methyl ester