(Z)-Cyclohexaneacrylic acid ethyl ester

Base Information

• Chemical Name: (Z)-Cyclohexaneacrylic acid ethyl ester
• CAS No.: 18521-02-3
• Molecular Formula: C11H18O2
• Molecular Weight: 182.263
• NSC Number: 244954
• Nikkaji Number: J1.428.263G
• Mol file: 18521-02-3.mol

Synonyms:18521-02-3;SCHEMBL14363086;NSC244954;NSC-244954;(Z)-Cyclohexaneacrylic acid ethyl ester

Chemical Property of (Z)-Cyclohexaneacrylic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0.0272mmHg at 25°C
• Boiling Point: 246.4°C at 760 mmHg
• Flash Point: 113.4°C
• Density: 1.019g/cm³
• 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:

99% ^*data from raw 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 (Z)-Cyclohexaneacrylic acid ethyl ester

There total 26 articles about (Z)-Cyclohexaneacrylic acid ethyl 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: 92.0%

ethyl 3-cyclohexyl-3-hydroxy-2-(trimethylsilyl)propanoate → (Z)-ethyl 3-cyclohexylacrylate (18521-02-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 12h; Time; Inert atmosphere;

DOI:10.1246/cl.160975

Reference yield: 86.0%

C32H46O7PPol + cyclohexanecarbaldehyde (2043-61-0) → (Z)-ethyl 3-cyclohexylacrylate (18521-02-3)

Guidance literature:

C₃₂H₄₆O₇PPol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere; solid phase reaction;

cyclohexanecarbaldehyde; In tetrahydrofuran; at -78 - 0 ℃; for 3h; optical yield given as %de; stereoselective reaction; Inert atmosphere; solid phase reaction;

DOI:10.1016/j.tetlet.2010.02.113

Reference yield: 85.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + cyclohexanecarbaldehyde (2043-61-0) → (E)-3-cyclohexyl-acrylic acid ethyl ester (17343-88-3) + (Z)-ethyl 3-cyclohexylacrylate (18521-02-3)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In 1,2-dimethoxyethane; at 0 - 20 ℃;

cyclohexanecarbaldehyde; In 1,2-dimethoxyethane; for 4h;

DOI:10.1021/ja068818t

upstream raw materials:

(E)-3-cyclohexyl-acrylic acid ethyl ester

cyclohexane

propynoic acid ethyl ester

1-bromocyclohexane

Downstream raw materials:

(Z)-3-cyclohexyl-2-propene-1-ol

(Z)-3-cyclohexylpropenoic acid

Refernces

• 1、 Murai, Yutaka,Nakagawa, Akira,Kojima, Satoshi. "Highly syn-selective elimination of peterson anti-adducts to give Z-α,β-unsaturated esters". supporting information. p. 228 - 231. Retrieved 2017/02/10.
• 2、 Joshi, Chetan,Kumar, Pawan,Behera, Babita,Barras, Alexandre,Szunerits, Sabine,Boukherroub, Rabah,Jain, Suman L.. "A graphene/hemin hybrid material as an efficient green catalyst for stereoselective olefination of aldehydes". . p. 100011 - 100017. Retrieved 2015/12/04.