(S)-2-HYDROXYMETHYLCYCLOHEXANONE

Base Information

• Chemical Name: (S)-2-HYDROXYMETHYLCYCLOHEXANONE
• CAS No.: 220199-90-6
• Molecular Formula: C7H12 O2
• Molecular Weight: 128.171
• Mol file: 220199-90-6.mol

Synonyms:(S)-2-HYDROXYMETHYLCYCLOHEXANONE

Chemical Property of (S)-2-HYDROXYMETHYLCYCLOHEXANONE

Chemical Property:

• PSA: 37.30000
• LogP: 0.73800

Purity/Quality:

99%min ^*data from raw suppliers

(S)-2-HYDROXYMETHYL-CYCLOHEXANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-HYDROXYMETHYLCYCLOHEXANONE

There total 9 articles about (S)-2-HYDROXYMETHYLCYCLOHEXANONE 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: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (S)-αlfa;-hydroxymethylcyclohexanone (220199-90-6)

Guidance literature:

formaldehyd; cyclohexanone; With L-threonine; magnesium sulfate; In tetrahydrofuran; water; at 20 ℃; for 120h; Sealed vial;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %ee; enantioselective reaction; Saturated solution;

DOI:10.1016/j.tet.2009.11.100

Reference yield: 37.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + acetaldehyde (75-07-0,9002-91-9) → (S)-αlfa;-hydroxymethylcyclohexanone (220199-90-6)

Guidance literature:

With water; (2S,4R)-4-((tert-butyldiphenylsilyl)oxy)pyrrolidine-2-carboxylic acid; at 20 ℃; for 90h;

DOI:10.1002/chem.200700363

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1-(Trimethylsilyloxy)cyclohexene (6651-36-1) → (S)-αlfa;-hydroxymethylcyclohexanone (220199-90-6) + (R)-2-(hydroxymethyl)cyclohexanone (784144-22-5)

Guidance literature:

With water; (S, S)-6,6’-bis(1-hydroxy-2,2-dimethylpropyl)-2,2’-bipyridine; scandium tris(trifluoromethanesulfonate); In acetonitrile; at -20 ℃; for 34h; Title compound not separated from byproducts;

DOI:10.1021/ja047896i

upstream raw materials:

formaldehyd

cyclohexanone

1-(Trimethylsilyloxy)cyclohexene

acetaldehyde

Downstream raw materials:

(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclohexanone

Refernces

• 1、 Pompeu, Yuri A.,Sullivan, Bradford,Walton, Adam Z.,Stewart, Jon D.. "Structural and catalytic characterization of pichia stipitis OYE 2.6, a useful biocatalyst for asymmetric alkene reductions". . p. 1949 - 1960. Retrieved 2012.
• 2、 Chino, Marco,D'Alonzo, Daniele,De Fenza, Maria,Esposito, Anna,Guaragna, Annalisa,Palumbo, Giovanni,Talarico, Giovanni,di Giovanni, Concetta. "A Stereoconvergent Tsuji–Trost Reaction in the Synthesis of Cyclohexenyl Nucleosides". . . Retrieved 2020/02/20.
• 3、 Ferrié, Laurent,Ferhi, Sabrina,Bernadat, Guillaume,Figadère, Bruno. "Toward the total synthesis of klaivanolide: Complete reinterpretation of its originally assigned structure". . p. 6183 - 6189. Retrieved 2015/03/30.