4-Pentenoic acid, 5-phenyl-, (Z)-

Base Information

• Chemical Name: 4-Pentenoic acid, 5-phenyl-, (Z)-
• CAS No.: 73850-25-6
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.215
• Mol file: 73850-25-6.mol

Synonyms:

Chemical Property of 4-Pentenoic acid, 5-phenyl-, (Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Pentenoic acid, 5-phenyl-, (Z)-

There total 32 articles about 4-Pentenoic acid, 5-phenyl-, (Z)- 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: 99.0%

dimethyl 2-cinnamylmalonate (3708-37-0) → 5-phenyl-4-pentenoic acid (17920-83-1,73850-25-6,28525-69-1)

Guidance literature:

dimethyl 2-cinnamylmalonate; With sodium hydroxide; water; In methanol; at 100 ℃;

With hydrogenchloride; water; In methanol; pH=2.0; Reflux;

DOI:10.1016/j.tet.2009.01.042

Reference yield: 88.0%

ethyl (4Z)-5-phenyl-4-pentenoate (121746-04-1) → (4Z)-5-phenylpent-4-enoic acid (17920-83-1,28525-69-1,73850-25-6)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 20 - 120 ℃; for 12h;

DOI:10.1002/anie.201808320

Reference yield: 58.0%

(3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6) + benzaldehyde (100-52-7) → (4E)-5-phenyl-4-pentenoic acid (28525-69-1) + (4Z)-5-phenylpent-4-enoic acid (17920-83-1,28525-69-1,73850-25-6)

Guidance literature:

(3-carboxypropyl)(triphenyl)phosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -60 ℃; for 0.583333h; Inert atmosphere;

benzaldehyde; In tetrahydrofuran; at -60 - 20 ℃; Overall yield = 87 %; Overall yield = 982 mg; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.090

upstream raw materials:

5-phenylpent-2-enoic acid

(E)-5-phenylpent-3-enoic acid

trans-cinnamylmalonic acid

3-Phenylpropenol

Downstream raw materials:

5-Phenylpentanoic acid

5-(bromo(phenyl)methyl)-dihydrofuran-2(3H)-one

Refernces

• 1、 Bond?i?, Aleksandra M.,Bond?i?, Bojan P.,D?ambaski, Zdravko,Kokotos, Christoforos G.,Triandafillidi, Ierasia. "Organocatalytic, Organic Oxidant Promoted, Enamine C?H Oxidation/Cyclopropanation Reaction". supporting information. p. 4002 - 4008. Retrieved 2021/07/06.
• 2、 Shen, Cong,Lu, Xiunan,Zhang, Jian,Ding, Liyuan,Sun, Yaling,Zhong, Guofu. "Bidentate auxiliary-directed alkenyl C-H allylation: Via exo-palladacycles: Synthesis of branched 1,4-dienes". supporting information. p. 13582 - 13585. Retrieved 2019/11/14.