cis-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]oxirane

Base Information

• Chemical Name: cis-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]oxirane
• CAS No.: 53226-67-8
• Molecular Formula: C₁₆H₁₄O
• Molecular Weight: 222.287
• Mol file: 53226-67-8.mol

Synonyms:

Chemical Property of cis-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]oxirane

There total 21 articles about cis-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]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: 70.0%

benzyltriphenylphosphonium bromide (1449-46-3) + (±)-3-phenyloxirane-2-carbaldehyde (5693-99-2,71403-94-6,99773-54-3,119951-98-3,121651-02-3,126720-47-6) → trans-2-phenyl-3-[(E)-2-phenyl-1-ethenyl] oxirane (53226-67-8,88430-52-8,97589-11-2,97589-12-3,143840-11-3)

Guidance literature:

benzyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -20 - 20 ℃;

(±)-3-phenyloxirane-2-carbaldehyde; In tetrahydrofuran; toluene; at -20 - 20 ℃;

DOI:10.1021/ol051653t

Reference yield: 70.0%

methyl (phenylmethyl)<(trimethylsilyl)methyl>sulfonium trifluoromethanesulfonate (119547-81-8) + 3-phenyl-propenal (104-55-2) → trans-2-phenyl-3-[(E)-2-phenyl-1-ethenyl] oxirane (53226-67-8,88430-52-8,97589-11-2,97589-12-3,143840-11-3)

Guidance literature:

With cesium fluoride; In 1,2-dimethoxyethane; at 40 ℃; for 12h;

DOI:10.1016/S0040-4020(01)86662-X

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → trans-2-phenyl-3-[(E)-2-phenyl-1-ethenyl] oxirane (53226-67-8,88430-52-8,97589-11-2,97589-12-3,143840-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

2.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3.1: KHMDS / toluene; tetrahydrofuran / -20 - 20 °C

3.2: 70 percent / toluene; tetrahydrofuran / -20 - 20 °C

With oxalyl dichloride; potassium hexamethylsilazane; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene; 2.1: Swern oxidation / 3.2: Wittig olefination;

DOI:10.1021/ol051653t

upstream raw materials:

methyl (phenylmethyl)<(trimethylsilyl)methyl>sulfonium trifluoromethanesulfonate

3-phenyl-propenal

(E)-3-phenylpropenal

sodium 2-benzylidene-1-tosylhydrazin-1-ide

Downstream raw materials:

(E)-3-phenylpropenal

meso-2,2'-bi(t,t-3,3-diphenyloxiranyl)

benzaldehyde