Ethyl 4-oxocyclohexanecarboxylate

Base Information

• Chemical Name: Ethyl 4-oxocyclohexanecarboxylate
• CAS No.: 17159-79-4
• Molecular Formula: C9H14O3
• Molecular Weight: 170.208
• Hs Code.: 29183000
• European Community (EC) Number: 628-731-6,921-755-0
• NSC Number: 250674
• UNII: 8L96JCJ75Y
• DSSTox Substance ID: DTXSID10312146
• Nikkaji Number: J1.221.537A
• Wikidata: Q72476478
• Metabolomics Workbench ID: 71661
• Mol file: 17159-79-4.mol

Synonyms:Ethyl 4-oxocyclohexanecarboxylate;17159-79-4;ethyl 4-oxocyclohexane-1-carboxylate;Ethyl 4-Cyclohexanonecarboxylate;Ethyl cyclohexanone-4-carboxylate;4-(Ethoxycarbonyl)cyclohexanone;4-Cyclohexanonecarboxylic Acid Ethyl Ester;4-(Ethoxycarbonyl)-1-cyclohexanone;4-oxo-cyclohexanecarboxylic acid ethyl ester;MFCD00013285;Cyclohexanecarboxylic acid, 4-oxo-, ethyl ester;8L96JCJ75Y;4-carboethoxycyclohexanone;4-ethoxycarbonylcyclohexanone;UNII-8L96JCJ75Y;4-oxocyclohexanecarboxylic acid ethyl ester;ethyl-4-oxocyclohexanecarboxylate;EC 628-731-6;ethyl 4-oxo-cyclohexanecarboxylate;Ethyl 4-oxocyclohexane carboxylate;Ethyl-4-oxo-cyclohexane carboxylate;NSC 250674;NSC-250674;4-cyclohexanone carboxylic acid ethyl ester;4-ketocyclohexanecarboxylic acid ethyl ester;NSC250674;4-carbethoxycyclohexanone;ethyl 4-oxo-cyclohexanoate;4-carboethoxy-cyclohexanone;SCHEMBL5483;4-ethoxycarbonyl cyclohexanone;4-ethoxycarbonyl-cyclohexanone;ethyl 4-oxo-cyclohexylcarboxylate;ethyl cyclohexan-4-onecarboxylate;DTXSID10312146;CHEBI:166505;Ethyl 4-ketocyclohexanecarboxylate;ethyl 4-oxocyclohexane-carboxylate;ethyl 4-oxocyclohexanecarbox-ylate;ethyl-4-oxo-cyclohexanecarboxylate;ethyl-4-oxocyclohexane carboxylate;BCP26831;ethyl 4-oxo-cyclo-hexanecarboxylate;ethyl 4-oxocyclohexan-1-carboxylate;STL183827;AKOS005254935;ethyl-4-oxo-1-cyclohexane carboxylate;AC-1078;AM81157;CS-W009093;PS-5511;SB40678;Ethyl 4-oxocyclohexanecarboxylate, 97%;4-oxocyclohexylcarboxylic acid ethyl ester;BP-12691;SY005687;4-oxocyclohexane carboxylic acid ethyl ester;A3785;C1530;FT-0618313;4-oxo-cyclo-hexanecarboxylic acid ethyl ester;4-oxo-cyclohexane carboxylic acid ethyl ester;EN300-64295;4-oxocyclohexane-1-carboxylic acid ethyl ester;4-OXOCYCLOHEXANECARBOXYLIC ACID, ETHYL ESTER;W-206013;F0001-0624;Z992759286;4-(Ethoxycarbonyl)cyclohexanone, Ethyl cyclohexanone-4-carboxylate

Chemical Property of Ethyl 4-oxocyclohexanecarboxylate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.0238mmHg at 25°C
• Melting Point: 221-226 °C
• Refractive Index: n20/D 1.461(lit.)
• Boiling Point: 248.8 °C at 760 mmHg
• Flash Point: 103.8 °C
• PSA: 43.37000
• Density: 1.083 g/cm³
• LogP: 1.30880
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Methanol
• Water Solubility.: insoluble
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 4-oxocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CCC(=O)CC1
• Uses: Ethyl 4-oxocyclohexanecarboxylate is a cyclohexanone derivative used in the study of cyclohexanone monooxygenase and its mutants as catalysts.It is also employed in the preparation of dopamine agonists1 and the skeleton of tetracyclic diterpenes. Employed in the preparation of dopamine agonists1 and the skeleton of tetracyclic diterpenes.2 Employed in the preparation of dopamine agonists and the skeleton of tetracyclic diterpenes.

Technology Process of Ethyl 4-oxocyclohexanecarboxylate

There total 33 articles about Ethyl 4-oxocyclohexanecarboxylate 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%

4-hydroxycyclohexyl carboxylic acid ethyl ester (3618-04-0,75877-66-6,17159-80-7) → ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4)

Guidance literature:

With jones reagent; In acetone;

DOI:10.1248/bpb.18.407

Reference yield: 98.0%

tetrapropylammonium perruthennate (114615-82-6) + 4-hydroxycyclohexyl carboxylic acid ethyl ester (3618-04-0,75877-66-6,17159-80-7) + 4-methylmorpholine N-oxide (7529-22-8) → ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4)

Guidance literature:

In ethyl acetate; acetonitrile;

Reference yield: 84.0%

4-oxocyclohexanecarboxylic acid (874-61-3) + ethanol (64-17-5) → ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4)

Guidance literature:

With thionyl chloride; In neat (no solvent); at 0 - 25 ℃; for 3h;

upstream raw materials:

4-oxocyclohexanecarboxylic acid

ethanol

trans-4-hydroxy-cyclohexane carboxylic acid ethyl ester

Ethyl 4-hydroxybenzoate

Downstream raw materials:

cyclohexanone-4-carboxylic acid ethyleneacetal

4-methoxy-3-cyclohexancarbonsaureethylester

C₉H₁₅⁽²⁾HO₃

4-oxocyclohexanecarboxylic acid

Refernces

• 1、 Jana, Anupam,Grela, Karol. "Mild Functionalization of Tetraoxane Derivatives via Olefin Metathesis: Compatibility of Ruthenium Alkylidene Catalysts with Peroxides". . p. 520 - 523. Retrieved 2017.
• 2、 Zhou, Hui,Bae, Han Yong,Leutzsch, Markus,Kennemur, Jennifer L.,Bécart, Diane,List, Benjamin. "The Silicon-Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes". supporting information. p. 13695 - 13700. Retrieved 2020/08/24.
• 3、 Watson, David W.,Gill, Matthew,Kemmitt, Paul,Lamont, Scott G.,Popescu, Mihai V.,Simpson, Iain. "An investigation into the role of 2,6-lutidine as an additive for the RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones". supporting information. p. 4479 - 4482. Retrieved 2018/11/23.