2-Cyano-2-cyclopentylideneacetamide

Base Information

• Chemical Name: 2-Cyano-2-cyclopentylideneacetamide
• CAS No.: 875-61-6
• Molecular Formula: C8H10 N2 O
• Molecular Weight: 150.18
• Hs Code.: 2926909090
• NSC Number: 98296
• DSSTox Substance ID: DTXSID50294811
• Mol file: 875-61-6.mol

Synonyms:2-cyano-2-cyclopentylideneacetamide;875-61-6;2-CYANO-2-CYCLOPENTYLIDENE-ACETAMIDE;acetamide, 2-cyano-2-cyclopentylidene-;NSC98296;cyclopentylidenecyanoacetamide;NCIOpen2_001617;Oprea1_695613;SCHEMBL11417303;DTXSID50294811;NSC-98296;STK411036;AKOS001443893;CS-0244806;EN300-29474;Z235361469

Chemical Property of 2-Cyano-2-cyclopentylideneacetamide

Chemical Property:

• Vapor Pressure: 3.97E-06mmHg at 25°C
• Boiling Point: 384.8°Cat760mmHg
• Flash Point: 186.5°C
• PSA: 66.88000
• Density: 1.203g/cm³
• LogP: 1.56618
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 150.079312947
• Heavy Atom Count: 11
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

2-Cyano-2-cyclopentylideneacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=C(C#N)C(=O)N)C1
• General Description: 2-Cyano-2-cyclopentylideneacetamide (also known as D1, a-Cyclopentaneacetamide, a-cyano-, or NSC 98296) is a key reactant used in the mild and efficient synthesis of functionalized spiro-substituted 1,2,3,4-tetrahydronicotinamides via the Michael reaction. Its nitrile group undergoes transformation into an amide under unusually mild conditions, facilitating the production of these compounds in good yields. Further studies are ongoing to explore the reaction mechanism, scope, and properties of the resulting products.

Technology Process of 2-Cyano-2-cyclopentylideneacetamide

There total 2 articles about 2-Cyano-2-cyclopentylideneacetamide 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: 64.0%

3-(aminocarbonyl)-1,3-dicyano-2-phenylspiro<3.4>oct-1-ene (113555-38-7) → Cyanocarbamidomethylenecyclopentane (875-61-6) + 3-Phenyl-2-propynonitrile (935-02-4)

Guidance literature:

In dichloromethane; for 1h; Irradiation;

DOI:10.1021/jo00274a021

Reference yield: 46.0%

2-amino-3,5-dicyano-6-phenyl-4H-pyran-4-spirocyclopentane (89809-98-3) → Cyanocarbamidomethylenecyclopentane (875-61-6) + 3-Phenyl-2-propynonitrile (935-02-4) + 3-(aminocarbonyl)-1,3-dicyano-2-phenylspiro<3.4>oct-1-ene (113555-38-7)

Guidance literature:

In dichloromethane; for 1h; Irradiation;

DOI:10.1021/jo00274a021

Reference yield: 69.0%

Cyanothioacetamide (7357-70-2) + Cyanocarbamidomethylenecyclopentane (875-61-6) → 1,2-dihydro-5,6-trimethylenespiro(cyclopentane-2-thieno[2,3-d]pyrimidine-4(3H)thione)

Guidance literature:

With 4-methyl-morpholine; In ethanol; at 20 ℃; for 0.5h;

DOI:10.1023/B:RUJO.0000034978.81993.bd

upstream raw materials:

3-(aminocarbonyl)-1,3-dicyano-2-phenylspiro<3.4>oct-1-ene

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

Downstream raw materials:

3-oxo-1-phenyl-3,5,6,7-tetrahydro-2H-cyclopenta[c]pyridine-4-carbonitrile

4-Cyano-2,3,5,6-tetrahydro-7H-cyclopenta<1,2-c>pyridin-3-one

7<1H>thioxo-2-phenyl cyclopenta pyridine-6-carbonitrile

3-(2-Oxo-propylsulfanyl)-1-phenyl-6,7-dihydro-5H-[2]pyrindine-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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