(S)-2-naphthylmethyl p-tolyl sulfoxide

Base Information

• Chemical Name: (S)-2-naphthylmethyl p-tolyl sulfoxide
• CAS No.: 1210452-02-0
• Molecular Formula: C₁₈H₁₆OS
• Molecular Weight: 280.39
• Mol file: 1210452-02-0.mol

Synonyms:

Chemical Property of (S)-2-naphthylmethyl p-tolyl sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-naphthylmethyl p-tolyl sulfoxide

There total 5 articles about (S)-2-naphthylmethyl p-tolyl sulfoxide 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:

1-methyl-4-[(2-(phenylsulfonyl)ethyl)sulfinyl]benzene (1308833-65-9) + 2-bromomethylnaphthyl bromide (939-26-4) → (S)-2-naphthylmethyl p-tolyl sulfoxide (1210452-02-0) + (R)-2-naphthylmethyl p-tolyl sulfoxide (1308833-81-9)

Guidance literature:

With (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide; In dichloromethane; water; toluene; at 0 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol2010962

Reference yield:

2-[(4-methylphenyl)sulfanyl]ethyl phenyl sulfone (32018-21-6) → (S)-2-naphthylmethyl p-tolyl sulfoxide (1210452-02-0) + (R)-2-naphthylmethyl p-tolyl sulfoxide (1308833-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dihydrogen peroxide / 2,2,2-trifluoroethanol; water / 0 - 20 °C

2: (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide / dichloromethane; water; toluene / 0 °C / Inert atmosphere

With (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; dihydrogen peroxide; sodium hydroxide; In dichloromethane; 2,2,2-trifluoroethanol; water; toluene;

DOI:10.1021/ol2010962

Reference yield:

para-thiocresol (106-45-6) → (S)-2-naphthylmethyl p-tolyl sulfoxide (1210452-02-0) + (R)-2-naphthylmethyl p-tolyl sulfoxide (1308833-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / dichloromethane / 20 h / 20 °C / Inert atmosphere

2: dihydrogen peroxide / 2,2,2-trifluoroethanol; water / 0 - 20 °C

3: (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; sodium hydroxide / dichloromethane; water; toluene / 0 °C / Inert atmosphere

With (1S,2S,4S,5R)-1-(anthracen-9-ylmethyl)-2-((R)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride; dihydrogen peroxide; potassium carbonate; sodium hydroxide; In dichloromethane; 2,2,2-trifluoroethanol; water; toluene;

DOI:10.1021/ol2010962

upstream raw materials:

(naphthalen-2-ylmethyl)(p-tolyl)thioether

1-methyl-4-[(2-(phenylsulfonyl)ethyl)sulfinyl]benzene

2-bromomethylnaphthyl bromide

2-[(4-methylphenyl)sulfanyl]ethyl phenyl sulfone

Refernces

• 1、 Santoni, Gabriella,Mba, Miriam,Bonchio, Marcella,Nugent, William A.,Zonta, Cristiano,Licini, Giulia. "Stereoselective control by face-to-face versus edge-to-face aromatic interactions: The case of C3-TiIV amino trialkolate sulfoxidation catalysts". experimental part. p. 645 - 654. Retrieved 2010/05/18.