3-CYCLOHEXYL-3-OXOPROPANENITRILE

Base Information

• Chemical Name: 3-CYCLOHEXYL-3-OXOPROPANENITRILE
• CAS No.: 62455-70-3
• Molecular Formula: C9H13NO
• Molecular Weight: 151.208
• Hs Code.: 2926909090
• Mol file: 62455-70-3.mol

Synonyms:cyanomethyl cyclohexyl ketone;3-Oxo-3-cyclohexyl-propionsaeure-nitril;3-cyclohexyl-3-oxo-propanenitrile;3-CYCLOHEXYL-3-OXO-PROPIONITRILE;3-Cyclohexyl-3-oxo-propionitril;

Chemical Property of 3-CYCLOHEXYL-3-OXOPROPANENITRILE

Chemical Property:

• Boiling Point: 249.6±13.0 °C(Predicted)
• PKA: 9.77±0.20(Predicted)
• PSA: 40.86000
• Density: 1.024±0.06 g/cm3(Predicted)
• LogP: 2.04948
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

β-oxo-Cyclohexanepropanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: β-oxo-Cyclohexanepropanenitrile is used in the preparation of pyrazoloquinazolinone derivatives as PARP-1 inhibitors. In addition, it is used in the preparation of benzoxazoyl amino cyanopyrimidines which act as negative allosteric mGlu5 modulators. Used in anxiety, depression and addiction treatment.

Technology Process of 3-CYCLOHEXYL-3-OXOPROPANENITRILE

There total 7 articles about 3-CYCLOHEXYL-3-OXOPROPANENITRILE 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: 98.0%

methyl cyclohexylcarboxylate (4630-82-4) + acetonitrile (75-05-8,26809-02-9) → 3-cyclohexyl-3-oxopropanenitrile (62455-70-3)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl cyclohexylcarboxylate; In tetrahydrofuran; at -78 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1021/acs.joc.8b02655

Reference yield: 80.0%

cyanoacetic acid (372-09-8) + cyclohexanylcarbonyl chloride (2719-27-9) → 3-cyclohexyl-3-oxopropanenitrile (62455-70-3)

Guidance literature:

cyanoacetic acid; With [2,2]bipyridinyl; n-butyllithium; magnesium sulfate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

cyclohexanylcarbonyl chloride; In tetrahydrofuran; methanol; hexane; at -78 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1016/j.tetlet.2011.03.009

Reference yield: 78.0%

ethyl cyclohexanecarboxylate (3289-28-9) + acetonitrile (75-05-8,26809-02-9) → 3-cyclohexyl-3-oxopropanenitrile (62455-70-3)

Guidance literature:

acetonitrile; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

ethyl cyclohexanecarboxylate; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

upstream raw materials:

methyl cyclohexylcarboxylate

acetonitrile

ethyl cyclohexanecarboxylate

cyanoacetic acid

Downstream raw materials:

2-Cyclohexyl-7-methyl-pyrazolo[1,5-a]pyrimidine-6-carboxylic acid

(Z)-2-(3,3-dimethyl-3,4-dihydro-(2H)-isoquinolin-1-ylidene)-1-cyclohexylethan-1-one

3-amino-1-cyclohexylpropan-1-ol

(S)-3-cyclohexyl-3-hydroxypropanenitrile

Refernces

• 1、 Boggu, Pulla Reddy,Venkateswararao, Eeda,Manickam, Manoj,Sharma, Niti,Kang, Jong Seong,Jung, Sang-Hun. "Identification of diphenylalkylisoxazol-5-amine scaffold as novel activator of cardiac myosin". . . Retrieved 2020/09/16.
• 2、 Pienaar, Daniel P.,Butsi, Kamogelo R.,Rousseau, Amanda L.,Brady, Dean. "A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones". supporting information. p. 2930 - 2935. Retrieved 2019/12/23.