2-Cyano-2-cyclohexylideneacetamide

Base Information

• Chemical Name: 2-Cyano-2-cyclohexylideneacetamide
• CAS No.: 704-16-5
• Molecular Formula: C9H12 N2 O
• Molecular Weight: 164.207
• European Community (EC) Number: 667-754-6
• NSC Number: 98308
• DSSTox Substance ID: DTXSID50990604
• Wikidata: Q27203619
• ChEMBL ID: CHEMBL1313697

Synonyms:2-cyano-2-cyclohexylideneacetamide;704-16-5;2-Cyano-2-cyclohexylidene-acetamide;MLS001030013;SMR000427202;NSC98308;cyclohexylidenecyanoacetamide;NCIOpen2_001654;Oprea1_248700;cid_263654;SCHEMBL2449598;CHEMBL1313697;BDBM55867;DTXSID50990604;CHEBI:116997;2-cyano-2cyclohexylidene-acetamide;2-cyclohexylidene-2-cyanoacetamide;HMS1775G18;HMS2810H08;2-cyano-2-cyclohexylidene-ethanamide;NSC-98308;STL326673;AKOS001082840;2-Cyano-2-cyclohexylideneethanimidic acid;EN300-17788;Q27203619;Z57036338

Chemical Property of 2-Cyano-2-cyclohexylideneacetamide

Chemical Property:

• Vapor Pressure: 2.43E-06mmHg at 25°C
• Boiling Point: 391.6°Cat760mmHg
• Flash Point: 190.6°C
• Density: 1.152g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.094963011
• Heavy Atom Count: 12
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=C(C#N)C(=O)N)CC1
• General Description: **2-Cyano-2-cyclohexylideneacetamide (also known as cyclohexylidenecyanoacetamide) is a reactive intermediate used in the synthesis of spiro-substituted 1,2,3,4-tetrahydronicotinamides via the Michael reaction under mild conditions. It participates in transformations where the nitrile group is converted into an amide, demonstrating utility in constructing functionalized heterocyclic frameworks. 2-cyano-2-cyclohexylideneacetamide's reactivity enables efficient coupling with acetoacetanilide or ethyl acetoacetate, yielding target products in good yields, highlighting its role as a versatile building block in organic synthesis.**

Technology Process of 2-Cyano-2-cyclohexylideneacetamide

There total 6 articles about 2-Cyano-2-cyclohexylideneacetamide 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: 78.0%

2-(cyclohexylidene)malononitrile (4354-73-8) → Cyanocarbamidomethylenecyclohexane (704-16-5)

Guidance literature:

With formic acid; palladium diacetate; at 20 ℃; for 7h;

DOI:10.1080/00397911.2018.1542496

Reference yield: 78.0%

ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2) + cyanoacetic acid amide (107-91-5) → Cyanocarbamidomethylenecyclohexane (704-16-5)

Guidance literature:

In ethanol; at 20 ℃; for 28h; Alkaline conditions;

DOI:10.1134/S1070428021110026

Reference yield: 30.0%

2-amino-3,5-dicyano-6-phenyl-4H-pyran-4-spirocyclohexane (89809-97-2) → Cyanocarbamidomethylenecyclohexane (704-16-5) + 3-Phenyl-2-propynonitrile (935-02-4) + 1,3-Dicyano-2-phenyl-spiro[3.5]non-2-ene-1-carboxylic acid amide (120446-36-8)

Guidance literature:

In dichloromethane; for 1h; Irradiation;

DOI:10.1021/jo00274a021

upstream raw materials:

cyclohexanone

cyanoacetic acid amide

2-amino-3,5-dicyano-6-phenyl-4H-pyran-4-spirocyclohexane

2-(cyclohexylidene)malononitrile

Downstream raw materials:

Spiropyrimidin-4-thion>

2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

3-azaspiro[5.5]undecane-2,4-dione

3-oxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

Refernces

Unusually mild and efficient synthesis of functionalized spiro-substituted 1,2,3,4-tetrahydro-nicotinamides by the michael reaction

10.1007/s10593-011-0854-5

The research details an unusually mild and efficient synthesis of functionalized spiro-substituted 1,2,3,4-tetrahydronicotinamides through the Michael reaction. The purpose of this study was to explore the transformation of the nitrile group into an amide group under mild conditions, which is typically challenging due to the need for rigorous conditions in such transformations. The researchers successfully synthesized these compounds using cyclopentylidenecyanoacetamide and cyclohexylidenecyanoacetamide as reactants with acetoacetanilide or ethyl acetoacetate, yielding the desired tetrahydronicotinamides in good yields. The study concluded with the successful synthesis of these compounds, and further investigation into the mechanism of the transformation, the scope of the reaction, and the chemical and biological properties of the products is ongoing. The chemicals used in the process include cyclopentylidenecyanoacetamide (1a), cyclohexylidenecyanoacetamide (1b), acetoacetanilide (2a), and ethyl acetoacetate (2b).

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