(5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one

Base Information

• Chemical Name: (5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one
• CAS No.: 88154-77-2
• Molecular Formula: C13H16O2S
• Molecular Weight: 236.335
• DSSTox Substance ID: DTXSID30455862
• Mol file: 88154-77-2.mol

Synonyms:88154-77-2;(5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one;(5R)-5-Methyl-2-(phenylsulfinyl)cyclohexanone;Cyclohexanone, 5-methyl-2-(phenylsulfinyl)-, (5R)-;(5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone;SCHEMBL9445759;DTXSID30455862;AKOS030240902;3(r)-methyl-6-phenylsulfinyl-cyclohexanone;A903930

Chemical Property of (5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one

Chemical Property:

• PSA: 53.35000
• LogP: 3.41760
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 236.08710092
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

95% ^*data from raw suppliers

(5R)-5-Methyl-2-(phenylsulfinyl)cyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(C(=O)C1)S(=O)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1CCC(C(=O)C1)S(=O)C2=CC=CC=C2
• Uses: (5R)-5-Methyl-2-(phenylsulfinyl)cyclohexanone (cas# 88154-77-2) is a compound useful in organic synthesis.

Technology Process of (5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one

There total 10 articles about (5R)-2-(Benzenesulfinyl)-5-methylcyclohexan-1-one 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%

(5R)-5-methyl-2-(phenylthio)cyclohexan-1-one (101693-93-0) → (5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one (88154-77-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃;

DOI:10.1021/ja00029a028

Reference yield: 84.0%

pulegone (89-82-7,90449-51-7) + thiophenol (108-98-5) → (5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one (88154-77-2)

Guidance literature:

pulegone; With dihydrogen peroxide; lithium hydroxide;

thiophenol; With sodium hydride;

With sodium perborate; acetic acid; enantioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02072

Reference yield:

(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one (308358-04-5,5730-01-8) → (5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one (88154-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / tetrahydrofuran / 18 h / Heating

2: 90 percent / mCPBA / CH₂Cl₂ / 2 h / -30 °C

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol026377m

upstream raw materials:

(5R)-5-methyl-2-(phenylthio)cyclohexan-1-one

(3R)-3-methylcyclohexanone

diphenyldisulfane

(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one

Downstream raw materials:

lycopodine

des-N-methyl-α-obscurine

(+)-fawcettimine

(R)-5-methyl-2-iodo-2-cyclohexen-1-one

Refernces

• 1、 Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.. "A concise asymmetric total synthesis of (+)-fawcettimine". supporting information. . Retrieved 2020/09/16.
• 2、 Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong. "Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization". supporting information. p. 4328 - 4331. Retrieved 2016/11/09.