Ethyl 2-cyano-2-cyclohexylideneacetate

Base Information

• Chemical Name: Ethyl 2-cyano-2-cyclohexylideneacetate
• CAS No.: 6802-76-2
• Molecular Formula: C11H15 N O2
• Molecular Weight: 193.246
• Hs Code.: 2926909090
• European Community (EC) Number: 229-878-5
• NSC Number: 10726
• DSSTox Substance ID: DTXSID70218211
• Nikkaji Number: J298.122J
• Mol file: 6802-76-2.mol

Synonyms:ethyl 2-cyano-2-cyclohexylideneacetate;6802-76-2;Ethyl cyanocyclohexylideneacetate;2-Cyano-2-cyclohexylideneacetic Acid Ethyl Ester;EINECS 229-878-5;ethyl cyano(cyclohexylidene)acetate;ethyl cyclohexylidenecyanoacetate;NSC10726;Ethyl2-cyano-2-cyclohexylideneacetate;NSC 10726;Cyano-Cyclohexylidene-Acetic Acid Ethyl Ester;SCHEMBL362584;DTXSID70218211;AMY16621;NSC-10726;AKOS003851219;Cyanocyclohexylideneacetic acid ethyl ester;FT-0665275;A19056;ETHYL ALPHA-(CYCLOHEXYLIDENE)CYANOACETATE;2-Cyano-2-cyclohexylidene-acetic acid ethyl ester;Acetic acid, 2-cyano-2-cyclohexylidene-, ethyl ester

Chemical Property of Ethyl 2-cyano-2-cyclohexylideneacetate

Chemical Property:

• Vapor Pressure: 0.000603mmHg at 25°C
• Boiling Point: 310.4°C at 760 mmHg
• Flash Point: 144.4°C
• PSA: 50.09000
• Density: 1.084g/cm³
• LogP: 2.33378
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 288

Purity/Quality:

98%min ^*data from raw suppliers

2-Cyano-2-cyclohexylideneacetic Acid Ethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C1CCCCC1)C#N
• Uses: 2-Cyano-2-cyclohexylideneacetic Acid Ethyl Ester can be used in the preparation of Gabapentin analogue.

Technology Process of Ethyl 2-cyano-2-cyclohexylideneacetate

There total 10 articles about Ethyl 2-cyano-2-cyclohexylideneacetate 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%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In neat liquid; at 20 ℃; for 0.133333h; Green chemistry;

DOI:10.1002/jccs.201200391

Reference yield: 63.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + pentan-3-one (96-22-0) → ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2)

Guidance literature:

With ammonium acetate; acetic acid; In benzene; for 6h; Dean-Stark; Reflux;

DOI:10.1039/c8ob00205c

Reference yield:

ethanol (64-17-5) + 2-cyano-2-cyclohexylideneacetic acid (37107-50-9) → ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2)

Guidance literature:

With hydrogenchloride; at 0 ℃;

upstream raw materials:

ethanol

2-cyano-2-cyclohexylideneacetic acid

acetamide

cyclohexanone

Downstream raw materials:

(1-Methylcyclohexyl)cyanessigsaeure-ethylester

1-carboxycyclohexylacetic acid

2-cyano-2-cyclohex-1-enyl-butyric acid ethyl ester

ethyl 2-cyano-2-(1-cyanocyclohexyl)acetate

Refernces

• 1、 Clark, Joseph R.,Dixon, Charlie F.,Feng, Kaibo,Han, Wei,Ide, Takafumi,Koch, Vanessa,Teng, Dawei,Wendell, Chloe I.,White, M. Christina. "Late-Stage Intermolecular Allylic C-H Amination". supporting information. p. 14969 - 14975. Retrieved 2021/10/01.
• 2、 Bhawal, Benjamin N.,Ehinger, Christian,Morandi, Bill,Reisenbauer, Julia C.. "Overcoming Selectivity Issues in Reversible Catalysis: A Transfer Hydrocyanation Exhibiting High Kinetic Control". supporting information. p. 10914 - 10920. Retrieved 2020/07/13.