Ethyl cyclohexenecarboxylate

Base Information

• Chemical Name: Ethyl cyclohexenecarboxylate
• CAS No.: 1617-22-7
• Molecular Formula: C9H14 O2
• Molecular Weight: 154.209
• Hs Code.: 2916209090
• European Community (EC) Number: 216-571-6
• DSSTox Substance ID: DTXSID00167223
• Nikkaji Number: J195.239K
• Wikidata: Q83036549
• Mol file: 1617-22-7.mol

Synonyms:Ethyl cyclohexenecarboxylate;1617-22-7;ethyl cyclohex-1-ene-1-carboxylate;ethyl cyclohexene-1-carboxylate;1-Cyclohexene-1-carboxylic acid, ethyl ester;EINECS 216-571-6;Cyclohexenecarboxylic acid, ethyl ester;SCHEMBL6049107;DTXSID00167223;ethyl 1-cyclohexene-1-carboxylate;ethylcyclohex-1-ene-1-carboxylate;AMY31886;BAA61722;AKOS006294483;cyclohexene-1-carboxylic acid ethyl ester;1-cyclohexene-1-carboxylic acid ethyl ester;EN300-760976

Chemical Property of Ethyl cyclohexenecarboxylate

Chemical Property:

• Vapor Pressure: 0.233mmHg at 25°C
• Boiling Point: 206.8°Cat760mmHg
• Flash Point: 75.1°C
• PSA: 26.30000
• Density: 1.015g/cm³
• LogP: 2.04990
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CCCCC1

Technology Process of Ethyl cyclohexenecarboxylate

There total 36 articles about Ethyl cyclohexenecarboxylate 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: 90.0%

methyl cyclohex-2-en-1-carboxylate (25662-37-7) → cyclohex-1-enecarboxylic acid ethyl ester (1617-22-7)

Guidance literature:

With sodium; In ethanol;

Reference yield: 89.0%

Ethyl 1-[(diethoxyphosphoryl)sulfanyl]-2-oxocyclohexanecarboxylate (533929-11-2) → cyclohex-1-enecarboxylic acid ethyl ester (1617-22-7) + Ethyl 2-[(diethoxyphosphoryl)oxy]-1-sulfanylcyclohexanecarboxylate

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 3h;

DOI:10.1039/b207700k

Reference yield: 79.0%

Ethyl 1-[(diethoxyphosphoryl)sulfanyl]-2-oxocyclohexanecarboxylate (533929-11-2) + methyl iodide (74-88-4) → cyclohex-1-enecarboxylic acid ethyl ester (1617-22-7) + Ethyl 7-thiabicyclo[4.1.0]heptane-1-carboxylate + Ethyl 2-[(diethoxyphosphoryl)oxy]-1-(methylsulfanyl)cyclohexanecarboxylate

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 20 ℃;

DOI:10.1039/b207700k

upstream raw materials:

ethanol

cyclohexene-1-carboxylic acid

cyclohex-1-enecarbonitrile

methyl 1-bromocyclohexanecarboxylate

Downstream raw materials:

(+/-)-(trans-2-ethoxycarbonyl-cyclohexyl)-malonic acid diethyl ester

2-(2-ethoxycarbonyl-cyclohexyl)-2-cyano-succinic acid diethyl ester

Ethyl 2-(α-cyanobenzyl)cyclohexane-1-carboxylate

ethyl cyclohexanecarboxylate

Refernces

• 1、 Godfrey,Ganem. "Reductive deoxygenation using hydridozirconium enolates: A new synthesis of α,β-unsaturated esters". . p. 7461 - 7464. Retrieved 1992.
• 2、 Hu, Xu-Hong,Zhang, Jian,Yang, Xiao-Fei,Xu, Yun-He,Loh, Teck-Peng. "Stereo- and chemoselective cross-coupling between two electron-deficient acrylates: An efficient route to (Z, E)-muconate derivatives". supporting information. p. 3169 - 3172. Retrieved 2015/03/30.
• 3、 Kim, Jinwoo,Chang, Sukbok. "Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions". supporting information. p. 2203 - 2207. Retrieved 2014/03/21.