(2R)-2-(2-Phenylethyl)oxirane

Base Information

• Chemical Name: (2R)-2-(2-Phenylethyl)oxirane
• CAS No.: 141036-66-0
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• UNII: VAT3878F36
• Nikkaji Number: J1.440.179B
• Wikidata: Q27896052
• Mol file: 141036-66-0.mol

Synonyms:(2R)-2-(2-Phenylethyl)oxirane;(R)-2-(2-Phenylethyl)oxirane;VAT3878F36;(3,4-Epoxybutyl)benzene, (R)-;(3,4-Epoxybutyl)benzene, (+)-;1,2-Epoxy-4-phenylbutane, (R)-;Oxirane, 2-(2-phenylethyl)-, (2R)-;UNII-VAT3878F36;141036-66-0;(R)-2-Phenethyloxirane;(R)-(3,4-epoxybutyl)benzene;SCHEMBL24137898;EN300-1863952;Q27896052

Chemical Property of (2R)-2-(2-Phenylethyl)oxirane

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 148.088815002
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(O1)CCC2=CC=CC=C2
• Isomeric SMILES: C1[C@H](O1)CCC2=CC=CC=C2

Technology Process of (2R)-2-(2-Phenylethyl)oxirane

There total 15 articles about (2R)-2-(2-Phenylethyl)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: 74.0%

4-Phenylbut-1-ene (768-56-9) → (R)-(2-phenylethyl)oxirane (141036-66-0)

Guidance literature:

With P₄₅₀tol-glucose dehydrogenase; In aq. phosphate buffer; ethanol; at 30 ℃; for 5h; enantioselective reaction; Microbiological reaction;

DOI:10.1039/c4cc03491k

Reference yield: 48.0%

1,2-Epoxy-4-phenylbutane (1126-76-7) → (R)-(2-phenylethyl)oxirane (141036-66-0)

Guidance literature:

1,2-Epoxy-4-phenylbutane; With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); acetic acid; In toluene; at 20 ℃; for 2h;

In water; toluene; at -10 - 20 ℃; for 24h;

DOI:10.1021/acs.orglett.8b03053

Reference yield:

(R)-1-chloro-4-phenylbutan-2-ol (153475-15-1) → (R)-(2-phenylethyl)oxirane (141036-66-0)

Guidance literature:

With sodium hydroxide; In diethyl ether; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)73959-1

upstream raw materials:

(R)-4-Phenyl-1-p-tolylsulfanyl-butan-2-ol

(R)-1-chloro-4-phenylbutan-2-ol

(2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate

4-Phenylbut-1-ene

Downstream raw materials:

C₁₆H₂₂O₂

C₁₄H₁₈O₂

C₁₄H₂₀O₂

Refernces

• 1、 Lin, Hui,Tang, Yanhong,Dong, Shuang,Lang, Ruibo,Chen, Hongge. "A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols". . p. 2145 - 2151. Retrieved 2020/04/17.
• 2、 Kubota, Koji,Yamamoto, Eiji,Ito, Hajime. "Copper(I)-catalyzed enantioselective nucleophilic borylation of aldehydes: An efficient route to enantiomerically enriched α-alkoxyorganoboronate esters". . p. 420 - 424. Retrieved 2015/01/30.