Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI)

Base Information

• Chemical Name: Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI)
• CAS No.: 235096-14-7
• Molecular Formula: C9H9 F O
• Molecular Weight: 152.168
• Mol file: 235096-14-7.mol

Synonyms:Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI)

Chemical Property of Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI)

Chemical Property:

• PSA: 12.53000
• LogP: 2.07110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI)

There total 3 articles about Oxirane, 2-(4-fluorophenyl)-2-methyl-, (2S)- (9CI) 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: 94.0%

1-(4-fluorophenyl)ethanone (403-42-9) + dimethylsulfoxonium methylide (70775-39-2,5367-24-8) → (2S)-2-(4-fluorophenyl)-2-methyloxirane (235096-14-7,235096-15-8)

Guidance literature:

With C₆₀H₃₆LaLi₃O₆; tris(2,4,6-trimethoxyphenyl)phosphine oxide; In tetrahydrofuran; at 20 - 23 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

DOI:10.1021/ja803864p

Reference yield:

2-(4-fluorophenyl)-1-propene (350-40-3) → p-fluoro-α-methylstyrene oxide (235096-15-8) + (2S)-2-(4-fluorophenyl)-2-methyloxirane (235096-14-7,235096-15-8)

Guidance literature:

With C₂₆H₃₆F₆FeN₆O₆S₂; C₃₀H₄₄N₄O₈; dihydrogen peroxide; In water; acetonitrile; at -30 ℃; for 0.5h; Overall yield = 81 %; Optical yield = 64 %ee; enantioselective reaction;

DOI:10.1039/c7sc00099e

Reference yield:

p-fluoro-α-methylstyrene oxide (2967-83-1,235096-15-8) → p-fluoro-α-methylstyrene oxide (235096-15-8) + (2S)-2-(4-fluorophenyl)-2-methyloxirane (235096-14-7,235096-15-8) + (S)-2-(4-Fluoro-phenyl)-propane-1,2-diol + (R)-2-(4-Fluoro-phenyl)-propane-1,2-diol

Guidance literature:

With Aspergillus niger LCP 521 epoxide hydrolase; In N,N-dimethyl-formamide; at 27 ℃; pH=8.0; Further Variations:; Reagents; Product distribution;

DOI:10.1021/jo982101+

upstream raw materials:

p-fluoro-α-methylstyrene oxide

1-(4-fluorophenyl)ethanone

dimethylsulfoxonium methylide

2-(4-fluorophenyl)-1-propene

Downstream raw materials:

(2R)-2-(4-fluorophenyl)-2-methyloxetane

Refernces

• 1、 Sone, Toshihiko,Lu, Gang,Matsunaga, Shigeki,Shibasaki, Masakatsu. "Catalytic asymmetric synthesis of 2,2-disubstituted oxetanes from ketones by using a one-pot sequential addition of sulfur ylide". supporting information; experimental part. p. 1677 - 1680. Retrieved 2009/06/30.
• 2、 Cleij,Archelas,Furstoss. "Microbiological transformations 43. Epoxide hydrolases as tools for the synthesis of enantiopure α-methylstyrene oxides: A new and efficient synthesis of (S)-ibuprofen". . p. 5029 - 5035. Retrieved 2007/10/03.