(R)-2-(3-vinylphenyl)oxirane

Base Information

• Chemical Name: (R)-2-(3-vinylphenyl)oxirane
• CAS No.: 1392406-50-6
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.189
• Mol file: 1392406-50-6.mol

Synonyms:(R)-2-(3-vinylphenyl)oxirane

Chemical Property of (R)-2-(3-vinylphenyl)oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(3-vinylphenyl)oxirane

There total 3 articles about (R)-2-(3-vinylphenyl)oxirane 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%

3-ethenylbenzaldehyde (19955-99-8) + 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ5,4Λ5-catenadi(phosphazene) (111324-03-9) → (R)-2-(3-vinylphenyl)oxirane (1392406-50-6)

Guidance literature:

With CF₃O₃S^(1-)*C₈₃H₇₁O₂S⁽¹⁺⁾; In tetrahydrofuran; at -78 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c2cc32101g

Reference yield: 47.0%

m-Divinylbenzene monoepoxide (105430-20-4) → (R)-2-(3-vinylphenyl)oxirane (1392406-50-6) + C10H10S

Guidance literature:

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; 3,4-dihydro-(1H)-quinoline-2-thione; In chloroform; at -20 - 20 ℃; for 53h; enantioselective reaction;

DOI:10.1021/jacs.6b01960

Reference yield:

3-ethenylbenzaldehyde (19955-99-8) → (R)-2-(3-vinylphenyl)oxirane (1392406-50-6) + C10H10S

Guidance literature:

Multi-step reaction with 2 steps

2: 3,4-dihydro-(1H)-quinoline-2-thione; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / chloroform / 53 h / -20 - 20 °C

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; 3,4-dihydro-(1H)-quinoline-2-thione; In chloroform; 1: |Corey-Tschaikosky Epoxidation;

DOI:10.1021/jacs.6b01960

upstream raw materials:

3-ethenylbenzaldehyde

1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ⁵,4Λ⁵-catenadi(phosphazene)

m-Divinylbenzene monoepoxide

Refernces

• 1、 Piccinini, Alessandro,Kavanagh, Sarah A.,Connon, Stephen J.. "Highly enantioselective ylide-mediated synthesis of terminal epoxides". supporting information; experimental part. p. 7814 - 7816. Retrieved 2012/09/05.