2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile

Base Information

• Chemical Name: 2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile
• CAS No.: 471905-01-8
• Molecular Formula: C20H18ClF2NO2S
• Molecular Weight: 409.884
• Mol file: 471905-01-8.mol

Synonyms:cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexaneacetaldehyde;cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetaldehyde;cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetonitrile;cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexaneacetonitrile;

Chemical Property of 2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile

Chemical Property:

• PSA: 66.31000
• LogP: 6.47208

Purity/Quality:

99% ^*data from raw suppliers

2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile

There total 10 articles about 2-((1s,4s)-4-(4-chlorophenylsulfonyl)-4-(2,5-difluorophenyl)cyclohexyl)acetonitrile 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: 95.0%

[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile (656810-84-3) + sodium metabisulfite → cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetonitrile (471905-01-8)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; n-heptane; Isopropyl acetate; water;

Reference yield: 94.0%

[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile (656810-84-3) → cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetonitrile (471905-01-8)

Guidance literature:

[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile; With L-Selectride; In tetrahydrofuran; at -60 - -55 ℃;

With sodium hydroxide; dihydrogen peroxide; sodium chloride; In tetrahydrofuran; at 5 ℃; Further stages.;

DOI:10.1039/b601647b

Reference yield:

2-[[(4-chlorophenyl)thio]methyl]-1,4-difluorobenzene (470716-52-0) → cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetonitrile (471905-01-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / sodium tungstate dihydrate; sulfuric acid; hydrogen peroxide / aliquat 336 / H₂O; toluene / 45 °C

2.1: 92 percent / acetic anhydride / dimethylformamide / 24.5 h / 60 °C

3.1: xylene / 16 h / 130 °C

4.1: 110 g / aq. HCl / xylene; tetrahydrofuran / 2 h / 50 °C

5.1: potassium tert-butoxide / tetrahydrofuran / 1 h / -5 °C

5.2: 97 percent / tetrahydrofuran / 20 h / 22 °C

6.1: 94 percent / L-selectride / tetrahydrofuran / 1.5 h / -60 °C

With hydrogenchloride; sodium tungstate; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; acetic anhydride; L-Selectride; Aliquat 336; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; xylene; 3.1: Diels-Alder reaction / 5.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jo070407n

upstream raw materials:

[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylidene]acetonitrile

2-[[(4-chlorophenyl)thio]methyl]-1,4-difluorobenzene

2-[[(4-chlorophenyl)sulfonyl]methyl]-1,4-difluorobenzene

4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanone

Downstream raw materials:

cis-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexylacetaldehyde

3-((1S,4R)-4-((4-chlorophenyl)sulfonyl)-4-(2,5- difluorophenyl)cyclohexyl)propanoic acid

cis-1-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexyl]-3-propanal

Refernces

• 1、 Scott, Jeremy P.,Mullens, Peter R.,Brewer, Sarah E.,Brands, Karel M.J.,Chilenski, Jennifer R.,Davies, Antony J.,Gibb, Andrew D.,Lieberman, David R.,Oliver, Steven F.,Dolling, Ulf-H.. "The conformational bias of aryl, arylsulfonyl geminally substituted tertiary carbon centers: Applications in substrate-based stereocontrol". . p. 1806 - 1810. Retrieved 2008/02/05.
• 2、 -. "Novel cyclohexyl sulphones". . . Retrieved 2008/06/13.