Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate

Base Information

• Chemical Name: Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate
• CAS No.: 67105-42-4
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.272
• European Community (EC) Number: 266-569-4
• NSC Number: 408235
• DSSTox Substance ID: DTXSID50983192
• Nikkaji Number: J310.196G
• Mol file: 67105-42-4.mol

Synonyms:67105-42-4;Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate;ethyl 2-cyano-2-(cyclohex-1-en-1-yl)propanoate;EINECS 266-569-4;64574-39-6;AI3-04924;1-Cyclohexene-1-acetic acid, alpha-cyano-alpha-methyl-, ethyl ester,(+-)-;NSC408235;SCHEMBL15973701;DTXSID50983192;1-Cyclohexene-1-acetic acid, alpha-cyano-alpha-methyl-, ethyl ester;NSC 408235;NSC-408235;SR-01000325575;SR-01000325575-1;alpha-Cyano-alpha-methyl-1-cyclohexene-1-acetic acid ethyl ester

Chemical Property of Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate

Chemical Property:

• Vapor Pressure: 0.000839mmHg at 25°C
• Boiling Point: 305.1°Cat760mmHg
• Flash Point: 141.4°C
• PSA: 50.09000
• Density: 1.069g/cm³
• LogP: 2.57978
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 324

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C#N)C1=CCCCC1

Technology Process of Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate

There total 7 articles about Ethyl 2-cyano-2-(cyclohex-1-enyl)propionate 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: 96.0%

ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2) + methyl iodide (74-88-4) → Methylcyclohexenylcyanoacetic acid ethyl ester (67105-42-4)

Guidance literature:

ethyl 2-cyano-2-cyclohexylideneacetate; With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; for 0.0166667h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

Reference yield: 84.0%

ethyl 1-cyclohexenylcyanoacetate (58567-40-1) + methyl iodide (74-88-4) → Methylcyclohexenylcyanoacetic acid ethyl ester (67105-42-4)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In N,N-dimethyl-formamide;

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + ethyl 2-cyanoacetate (105-56-6) → Methylcyclohexenylcyanoacetic acid ethyl ester (67105-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: L-proline / ethanol / 20 - 80 °C

2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C

2.2: 3 h / 20 °C

With potassium tert-butylate; L-proline; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jacs.1c06335

upstream raw materials:

sodium ethanolate

ethyl 2-cyano-2-cyclohexylideneacetate

methyl iodide

ethyl 1-cyclohexenylcyanoacetate

Downstream raw materials:

hexabarbital