Ethyl 3-phenylcrotonate

Base Information

• Chemical Name: Ethyl 3-phenylcrotonate
• CAS No.: 945-93-7
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• Hs Code.: 2916399090
• Nikkaji Number: J565.197B,J818.761D
• NSC Number: 20769
• Mol file: 945-93-7.mol

Synonyms:Ethyl 3-phenylcrotonate;ethyl (2Z)-3-phenylbut-2-enoate;ethyl (Z)-3-phenylbut-2-enoate;SCHEMBL2205704;NSC20769;NSC-20769;AKOS037629454;LS-12233;(Z)-3-phenyl-but-2-enoic acid ethyl ester;EN300-1460171;13979-22-1

Chemical Property of Ethyl 3-phenylcrotonate

Chemical Property:

• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 268.5 °C at 760 mmHg
• Flash Point: 143.7 °C
• PSA: 26.30000
• Density: 1.018 g/cm³
• LogP: 2.65300
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl3-Phenylbut-2-enoate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24-25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C1=CC=CC=C1
• Isomeric SMILES: CCOC(=O)/C=C(/C)\C1=CC=CC=C1

Technology Process of Ethyl 3-phenylcrotonate

There total 151 articles about Ethyl 3-phenylcrotonate 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: 100.0%

ethyl (E)-3-phenylbut-2-enoate (945-93-7,13979-22-1,1504-72-9) → ethyl (Z)-3-phenylbut-2-enoate (945-93-7,1504-72-9,13979-22-1)

Guidance literature:

With riboflavin; In acetonitrile; at 20 ℃; for 24h; diastereoselective reaction; Irradiation;

DOI:10.1021/jacs.5b07136

Reference yield: 99.0%

(2E)-ethyl 3-chloro-2-iodobut-2-enoate (888039-38-1) + phenylboronic acid (98-80-6) → biphenyl (92-52-4,1594-86-1) + ethyl (E)-3-phenylbut-2-enoate (945-93-7,13979-22-1,1504-72-9)

Guidance literature:

With caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,4-dioxane; for 4h; Heating;

DOI:10.1021/jo8008325

Reference yield: 98.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + acetophenone (98-86-2) → ethyl (E)-3-phenylbut-2-enoate (945-93-7,13979-22-1,1504-72-9)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃;

acetophenone; In tetrahydrofuran; mineral oil; at 20 ℃;

DOI:10.1021/acs.joc.7b01248

upstream raw materials:

ethyl bromoacetate

acetophenone

<1-Phenyl-aethyliden>-triphenyl-phosphoran

ethyl 2-(ethoxythiocarbonylthio)acetate

Downstream raw materials:

3,4,6-trimethyl-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester

1-<(trimethylsilyl)oxy>-1-ethoxy-3-phenyl-1,3-butadiene

6-Benzoyl-5-furan-2-yl-3-phenyl-cyclohex-2-enone

3-phenyl-1-butanol

Refernces

• 1、 Fung, Jonathan,Duong, Truc-Vi,Braceros, Keean C. A.,Brooks, Marilyn L.,Schloesser-Lingscheit, Katie,Tagawa, Tristen K. S.,Wilson, Johanna M.,Jones, Kevin K.,Valente, Edward J.. "Arylpyran Pseudoacid Racemization: Rate Estimation and Structural Influences". . p. 14 - 41. Retrieved 2020/04/29.
• 2、 Ren, Xiang,Lu, Zhan. "Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin". supporting information. p. 8370 - 8374. Retrieved 2021/11/01.