Dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate
• CAS No.: 36650-44-9
• Molecular Formula: C20H20O4
• Molecular Weight: 324.376
• NSC Number: 135152
• DSSTox Substance ID: DTXSID30300161
• Nikkaji Number: J3.546.648G
• Mol file: 36650-44-9.mol

Synonyms:36650-44-9;dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate;NSC135152;DTXSID30300161;NSC-135152

Chemical Property of Dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 1.13E-07mmHg at 25°C
• Boiling Point: 432.2°Cat760mmHg
• Flash Point: 212.7°C
• Density: 1.181g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 324.13615911
• Heavy Atom Count: 24
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(C(C1C(=O)OC)C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate

There total 60 articles about Dimethyl 3,4-diphenylcyclobutane-1,2-dicarboxylate 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%

methanol (67-56-1) + methyl β-D-xylopyranoside 2,4-truxinate → dimethyl (1R,2S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate (36650-44-9)

Guidance literature:

With thionyl chloride; at 20 ℃; for 72h;

DOI:10.1039/b609115f

Reference yield: 81.0%

methyl cinnamate (103-26-4,1754-62-7) → dimethyl (1R,2S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate (36650-44-9) + rac-1,2-dimethyl (1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate (36650-44-9,52305-38-1,52305-39-2,57287-73-7,57287-74-8,58691-75-1,58691-76-2,64666-08-6,64666-09-7,64666-10-0,114180-12-0)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 72h; Overall yield = 89%; diastereoselective reaction; Schlenk technique; Irradiation; Inert atmosphere;

DOI:10.1039/c7cc06710k

Reference yield: 81.0%

methyl cinnamate (103-26-4,1754-62-7) → dimethyl (1R,2S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate (36650-44-9) + rac-1,2-dimethyl (1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylate (36650-44-9,52305-38-1,52305-39-2,57287-73-7,57287-74-8,58691-75-1,58691-76-2,64666-08-6,64666-09-7,64666-10-0,114180-12-0)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 72h; Overall yield = 89%; diastereoselective reaction; Schlenk technique; Irradiation; Inert atmosphere;

DOI:10.1039/c7cc06710k

upstream raw materials:

diazomethane

β-truxinic acid

sodium trans-cinnamate

methyl (2Z)-3-phenylprop-2-enoate

Downstream raw materials:

r-1,t-2-dimethyl-t-3,c-3,4-diphenylcyclobutane

(1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid

μ-truxinic acid

β-truxinic acid