(2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one

Base Information

• Chemical Name: (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one
• CAS No.: 637042-66-1
• Molecular Formula: C₁₅H₁₁ClO₂
• Molecular Weight: 258.704
• Mol file: 637042-66-1.mol

Synonyms:(2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one

Chemical Property of (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one

There total 12 articles about (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-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: 99.0%

(E)-1-(4-chlorophenyl)-3-phenyl-2-propen-1-one (22966-22-9) → (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one (637042-66-1)

Guidance literature:

With C₃₃H₃₄N₃O₂⁽¹⁺⁾*Br^(1-); dihydrogen peroxide; sodium hydroxide; In diethyl ether; toluene; at 5 ℃; for 1h; enantioselective reaction;

DOI:10.1021/acs.orglett.0c03272

Reference yield: 99.0%

4'-chlorochalcone (956-02-5) → (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one (637042-66-1)

Guidance literature:

With tert.-butylhydroperoxide; [(Me₃Si)₂N]₃Yb^III(μ-Cl)Li(THF)₃; (S)-2,4-di-tert-butyl-6-[[2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]methyl]phenol; In tetrahydrofuran; at 20 ℃; for 4h; enantioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00833

Reference yield: 85.0%

4'-chlorochalcone (956-02-5) → (2S,3R)-2,3-epoxy-1-(4-chlorophenyl)-3-phenylpropan-1-one (637042-66-1) + trans-(2R,3S)-2,3-epoxy-3-phenyl-1-(4-chlorophenyl)propan-1-one (32157-73-6,40327-53-5,67175-58-0,130007-85-1)

Guidance literature:

4'-chlorochalcone; With C₂₀H₂₄F₆MnN₄O₆S₂; In acetonitrile; at 20 ℃; for 0.05h; Inert atmosphere;

With peracetic acid; In acetonitrile; at 20 ℃; for 1.33333h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.jorganchem.2012.03.034

upstream raw materials:

(E)-1-(4-chlorophenyl)-3-phenyl-2-propen-1-one

para-chloroacetophenone

benzaldehyde

4'-chlorochalcone

Refernces

• 1、 Zhang, Lu-Wen,Wang, Li,Ji, Nan,Dai, Si-Yang,He, Wei. "Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis". supporting information. . Retrieved 2021/03/15.
• 2、 Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata. "Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts". supporting information. . Retrieved 2020/11/13.