ethyl (4Z)-5-phenyl-4-pentenoate

Base Information

• Chemical Name: ethyl (4Z)-5-phenyl-4-pentenoate
• CAS No.: 121746-04-1
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.269
• Mol file: 121746-04-1.mol

Synonyms:ethyl (4Z)-5-phenyl-4-pentenoate

Chemical Property of ethyl (4Z)-5-phenyl-4-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (4Z)-5-phenyl-4-pentenoate

There total 48 articles about ethyl (4Z)-5-phenyl-4-pentenoate 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: 93.0%

ethyl acetate (141-78-6) + Cinnamyl bromide (4392-24-9) → (E)-ethyl 5-phenylpent-4-enoate (22768-07-6,121746-04-1,93845-04-6)

Guidance literature:

ethyl acetate; With copper(l) iodide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Cinnamyl bromide; In tetrahydrofuran; hexane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jacs.1c07702

Reference yield: 91.0%

[(1-Ethoxycyclopropyl)oxy]trimethylsilane (27374-25-0) + (E)-phenylethenyl(phenyl)iodonium tetrafluoroborate → (E)-ethyl 5-phenylpent-4-enoate (22768-07-6,121746-04-1,93845-04-6)

Guidance literature:

palladium diacetate; In 1,2-dimethoxyethane; water; at 30 ℃; for 1h;

DOI:10.1016/S0040-4039(97)00230-X

Reference yield: 84.0%

bromobenzene (108-86-1,52753-63-6) + ethyl 4-pentenoate (1968-40-7) → (E)-ethyl 5-phenylpent-4-enoate (22768-07-6,121746-04-1,93845-04-6) + ethyl 4-phenyl-4-pentenoate (78687-92-0)

Guidance literature:

With cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane; sodium acetate; bis(η3-allyl-μ-chloropalladium(II)); In N,N-dimethyl-formamide; at 130 ℃; for 20h;

DOI:10.1016/j.jorganchem.2007.01.056

upstream raw materials:

5-chloro-5-phenyl-valeric acid ethyl ester

sodium tert-pentoxide

Ethyl 3-bromopropionate

(2-phenylvinyl)tributylstannane

Downstream raw materials:

(S,E)-3-(nitromethyl)-5-phenylpent-4-enal

(S,E)-5-(4-methoxyphenyl)-3-(nitromethyl)pent-4-enal

5-phenyl-4-penten-1-ol

(2E,6E)-2-(3,4-dihydroxybenzylidene)-3-oxo-7-phenylhept-6-enenitrile

Refernces

• 1、 Romine, Andrew M.,Yang, Kin S.,Karunananda, Malkanthi K.,Chen, Jason S.,Engle, Keary M.. "Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis". . p. 7626 - 7640. Retrieved 2019.
• 2、 Wang, Mang,Gao, Lian Xun,Yue, Wei,Mai, Wen Peng. "Reagent-Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources". . p. 1023 - 1032. Retrieved 2004.
• 3、 Kang, Suk-Ku,Yamaguchi, Tokutaro,Ho, Pil-Su,Kim, Won-Yeob,Yoon, Seok-Keun. "Palladium-catalyzed coupling and carbonylative coupling of silyloxy compounds with hypervalent iodonium salts". . p. 1947 - 1950. Retrieved 1997.
• 4、 Crawford, Evan T.,De Jesús Cruz, Pedro,Johnson, Jeffrey S.,Liu, Shubin. "Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile". supporting information. p. 16264 - 16273. Retrieved 2021/10/21.
• 5、 Han, Jiyao,Sun, Xiaowei,Wang, Xiao,Wang, Qiong,Hou, Shenghuai,Song, Xin,Wei, Yingqin,Wang, Rongyu,Ji, Wenhua. "Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction". supporting information. p. 1480 - 1484. Retrieved 2020/03/13.