(E)-Ethyl 3-cyclohexylacrylate

Base Information

• Chemical Name: (E)-Ethyl 3-cyclohexylacrylate
• CAS No.: 17343-88-3
• Molecular Formula: C11H18O2
• Molecular Weight: 182.263
• Hs Code.: 2916209090
• NSC Number: 244952
• Nikkaji Number: J1.952.597J,J924.723H
• Mol file: 17343-88-3.mol

Synonyms:(E)-Ethyl 3-cyclohexylacrylate;17343-88-3;Ethyl (E)-3-cyclohexyl-2-propenoate;ethyl 3-cyclohexylacrylate;ethyl (E)-3-cyclohexylprop-2-enoate;(E)-3-Cyclohexyl-acrylic acid ethyl ester;Ethyl(E)-3-cyclohexyl-2-propenoate;ETHYL (2E)-3-CYCLOHEXYLPROP-2-ENOATE;NSC244952;SCHEMBL1581948;ethyl (2E)-3-cyclohexylacrylate;SLGCKLRNFQEFEO-CMDGGOBGSA-N;Cyclohexaneacrylic acid ethyl ester;18521-02-3;MFCD09839402;AKOS006327307;NSC-244952;(E)-Cyclohexaneacrylic acid ethyl ester;LS-09564;EN300-1455936

Chemical Property of (E)-Ethyl 3-cyclohexylacrylate

Chemical Property:

• Vapor Pressure: 0.0272mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 246.4 °C at 760 mmHg
• Flash Point: 113.4 °C
• PSA: 26.30000
• Density: 1.019 g/cm³
• LogP: 2.68600
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 182.130679813
• Heavy Atom Count: 13
• Complexity: 179

Purity/Quality:

98% ^*data from raw suppliers

Ethyl 3-cyclohexylacrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1CCCCC1
• Isomeric SMILES: CCOC(=O)/C=C/C1CCCCC1

Technology Process of (E)-Ethyl 3-cyclohexylacrylate

There total 42 articles about (E)-Ethyl 3-cyclohexylacrylate 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: 98.0%

diazoacetic acid ethyl ester (623-73-4) + cyclohexanecarbaldehyde (2043-61-0) → (E)-3-cyclohexyl-acrylic acid ethyl ester (17343-88-3)

Guidance literature:

With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane; In toluene; at 110 ℃; for 12h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c1cc16747b

Reference yield: 97.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + cyclohexanecarbaldehyde (2043-61-0) → (E)-3-cyclohexyl-acrylic acid ethyl ester (17343-88-3)

Guidance literature:

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; for 4h; optical yield given as %de; stereoselective reaction; Inert atmosphere; neat (no solvent);

DOI:10.1039/c1gc15134g

Reference yield: 93.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-cyclohexyl-2-propenal (37868-74-9,147159-44-2,935-03-5) → (E)-3-cyclohexyl-acrylic acid ethyl ester (17343-88-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol1021756

upstream raw materials:

8-oxabicyclo[5.1.0]octane

tributyl(methoxycarbonylmethylene)phosphonium bromide

cyclohexane

propynoic acid ethyl ester

Downstream raw materials:

(Z)-ethyl 2-bromo-3-cyclohexylpropenoate

(S)-ethyl 3-cyclohexyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

C₂₁H₃₁NO₄S

Refernces

• 1、 Matui, Syuichi,Tanaka, Kazuhiko,Kaji, Aritsune. "Stereoselective Synthesis of 2-Alkenoic Esters from Carbonyl Compounds and the Dilithio Derivative of Ethyl Mercaptoacetate". . p. 127 - 128. Retrieved 1983.
• 2、 Fujimura, Osamu,Honma, Takashi. "Olefination of aldehydes by ethyl diazoacetate catalyzed by a Ruthenium(II) complex". . p. 625 - 626. Retrieved 1998.
• 3、 Hong, Chang Whee,Lee, Yong Jin,An, Duk Keun. "A One-Pot Synthesis of α,β-Unsaturated Esters From Esters". . p. 1121 - 1125. Retrieved 2021/06/01.
• 4、 Inaba, Ryoto,Kawashima, Ikuo,Fujii, Toshiki,Yumura, Takashi,Imoto, Hiroaki,Naka, Kensuke. "Systematic Study on the Catalytic Arsa-Wittig Reaction". supporting information. p. 13400 - 13407. Retrieved 2020/09/21.