2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester

Base Information

• Chemical Name: 2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester
• CAS No.: 101723-21-1
• Molecular Formula: C18H16O2
• Molecular Weight: 264.31800
• European Community (EC) Number: 682-997-8
• DSSTox Substance ID: DTXSID30296999
• Mol file: 101723-21-1.mol

Synonyms:101723-21-1;2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester;DTXSID30296999

Chemical Property of 2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester

Chemical Property:

• PSA: 26.30000
• LogP: 3.84750
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 264.115029749
• Heavy Atom Count: 20
• Complexity: 336

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester

There total 5 articles about 2,4-Pentadienoic acid, 5,5-diphenyl-, methyl ester 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:

3,3-diphenyl-2-propenal (1210-39-5) + Methyl diethylphosphonoacetate (1067-74-9) → (E)-methyl 5,5-diphenylpenta-2,4-dienoate (101723-21-1)

Guidance literature:

Methyl diethylphosphonoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

3,3-diphenyl-2-propenal; In tetrahydrofuran; at 0 ℃; for 0.5h;

With water; In tetrahydrofuran;

Reference yield:

(4Z)-methyl 5-((diethoxyphosphoryl)oxy)-5-phenylpenta-2,4-dienoate + phenylboronic acid (98-80-6) → C18H16O2 + (E)-methyl 5,5-diphenylpenta-2,4-dienoate (101723-21-1)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate; tricyclohexylphosphine; In tetrahydrofuran; at 110 ℃; for 24h; Overall yield = 68 %; Overall yield = 17.9 mg; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201506437

Reference yield:

1-bromo-2-(1-phenylpropen-1-yl)benzene (24892-82-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (E)-methyl 5,5-diphenylpenta-2,4-dienoate (101723-21-1) + methyl (Z)-5,5-diphenylpenta-2,4-dienoate + methyl (E)-3-(2-(1-phenylvinyl)phenyl)acrylate

Guidance literature:

With tris(o-methoxyphenyl)phosphine; palladium diacetate; cesium fluoride; In tetrahydrofuran; at 100 ℃; for 3h; Reagent/catalyst; stereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201801963

upstream raw materials:

benzophenone

methyl-4-bromo-2-butenoate

3,3-diphenyl-2-propenal

Methyl diethylphosphonoacetate

Downstream raw materials:

(E)-5,5-diphenyl-2,4-pentadienoic acid

5,5-diphenyl-valeric acid methyl ester

(E)-5,5-diphenylpenta-2,4-dien-1-ol

5,5-diphenylpentanoic acid

Refernces

• 1、 Hu, Xu-Hong,Yang, Xiao-Fei,Loh, Teck-Peng. "Selective Alkenylation and Hydroalkenylation of Enol Phosphates through Direct C-H Functionalization". supporting information. p. 15535 - 15539. Retrieved 2016/01/26.