1'-Hydroxy-bicyclohexyl-1-carbonitrile

Base Information

• Chemical Name: 1'-Hydroxy-bicyclohexyl-1-carbonitrile
• CAS No.: 57527-71-6
• Molecular Formula: C₁₃H₂₁NO
• Molecular Weight: 207.316
• DSSTox Substance ID: DTXSID80464727
• Nikkaji Number: J2.024.520D
• Wikidata: Q82290181
• Mol file: 57527-71-6.mol

Synonyms:57527-71-6;1'-HYDROXY-BICYCLOHEXYL-1-CARBONITRILE;1-(1-hydroxycyclohexyl)cyclohexane-1-carbonitrile;1'-Hydroxy[1,1'-bicyclohexyl]-1-carbonitrile;DTXSID80464727;AKOS015963105

Chemical Property of 1'-Hydroxy-bicyclohexyl-1-carbonitrile

Chemical Property:

• PSA: 44.02000
• LogP: 3.15568
• Solubility.: Chloroform, Diethyl Ether, Ethylacetate
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 207.162314293
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

99%min ^*data from raw suppliers

1''-Hydroxy[1,1''-bicyclohexyl]-1-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)(C#N)C2(CCCCC2)O
• Uses: 1''-Hydroxy[1,1''-bicyclohexyl]-1-carbonitrile is an intermediate in teh synthesis of 1'',2''-Dehydro Dicyclomine (D229530) which is an impurity of Dicyclomine (D439300, HCl); a compound used as a gastrointestinal antispasmodic antacid.

Technology Process of 1'-Hydroxy-bicyclohexyl-1-carbonitrile

There total 7 articles about 1'-Hydroxy-bicyclohexyl-1-carbonitrile 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: 92.0%

1-(phenylsulfinyl)cyclohexanecarbonitrile (1360557-39-6) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1'-hydroxy-[1,1'-bi(cyclohexane)]-1-carbonitrile (57527-71-6)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1002/anie.201105630

Reference yield: 74.0%

1-(dimethylsilyl)cyclohexanecarbonitrile (1446698-42-5) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1'-hydroxy-[1,1'-bi(cyclohexane)]-1-carbonitrile (57527-71-6)

Guidance literature:

1-(dimethylsilyl)cyclohexanecarbonitrile; cyclohexanone; With magnesium chloride; In dimethyl sulfoxide; at 30 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In methanol; water; dimethyl sulfoxide; for 0.166667h; Inert atmosphere;

DOI:10.1021/ol401663u

Reference yield: 73.0%

1-bromocyclohexane-1-carbonitrile (676132-35-7) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 1'-hydroxy-[1,1'-bi(cyclohexane)]-1-carbonitrile (57527-71-6)

Guidance literature:

With isopropylmagnesium bromide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/ol036202s

upstream raw materials:

cyclohexanone

(cyanocyclohexyl)lithium

cyclohexane carbonitrile

cyclohexane-1,1-dicarbonitrile

Downstream raw materials:

Bicyclohexyl-1'-ene-1-carboxylic acid amide

Bicyclohexyl-1'-ene-1-carbonitrile

Refernces

• 1、 Jinzaki, Takaaki,Arakawa, Mitsuru,Kinoshita, Hidenori,Ichikawa, Junji,Miura, Katsukiyo. "Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones". supporting information. p. 3750 - 3753. Retrieved 2013/08/23.
• 2、 Fleming, Fraser F.,Zhang, Zhiyu,Liu, Wang,Knochel, Paul. "Metalated nitriles: Organolithium, -magnesium? and -copper exchange of α-halonitriles". . p. 2200 - 2205. Retrieved 2007/10/03.