2-Phenyl-3-vinyloxirane

Base Information

• Chemical Name: 2-Phenyl-3-vinyloxirane
• CAS No.: 20248-57-1
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• DSSTox Substance ID: DTXSID00454544
• Nikkaji Number: J660.945G
• Mol file: 20248-57-1.mol

Synonyms:2-phenyl-3-vinyloxirane;2-ethenyl-3-phenyloxirane;20248-57-1;SCHEMBL5057401;DTXSID00454544;JREKMQNEGCRTPI-UHFFFAOYSA-N;AKOS015905921

Chemical Property of 2-Phenyl-3-vinyloxirane

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC1C(O1)C2=CC=CC=C2

Technology Process of 2-Phenyl-3-vinyloxirane

There total 16 articles about 2-Phenyl-3-vinyloxirane 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: 86.0%

2,3-epoxy-3-phenylpropanal (71403-94-6) + diazomethyl-trimethyl-silane (18107-18-1) → 2-phenyl-3-vinyloxirane (20248-57-1)

Guidance literature:

With Rh(PPh₃)3Cl; triphenylphosphine; In tetrahydrofuran; isopropyl alcohol; at 25 ℃; for 1h;

DOI:10.1002/1521-3773(20010803)40:15<2887::AID-ANIE2887>3.0.CO;2-Q

Reference yield: 80.0%

allyl bromide (106-95-6) + benzyl alcohol (100-51-6,185532-71-2) → 2-phenyl-3-vinyloxirane (20248-57-1)

Guidance literature:

benzyl alcohol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 2h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 4h; Inert atmosphere;

allyl bromide; With sodium hydroxide; In propan-1-ol; water; at 40 ℃; for 18h;

Reference yield: 75.0%

phenyldiazomethane (908094-04-2) + acrolein (107-02-8,25068-14-8) → 2-phenyl-3-vinyloxirane (20248-57-1)

Guidance literature:

With dirhodium tetraacetate; dimethylsulfide; In dichloromethane;

upstream raw materials:

R*,R*-3-methylthio-4-phenyl-1-butenol-4

allyl(dimethyl)sulfonium bromide

benzaldehyde

diisobutyl telluronium allylide

Downstream raw materials:

((E)-3-Methylsulfanyl-propenyloxymethyl)-benzene

1-Phenyl-1-butanol

(Z)-N-benzylidene-1-phenylbut-2-en-1-amine

Refernces

• 1、 Illa, Ona,Namutebi, Mariam,Saha, Chandreyee,Ostovar, Mehrnoosh,Chen, C. Chun,Haddow, Mairi F.,Nocquet-Thibault, Sophie,Lusi, Matteo,McGarrigle, Eoghan M.,Aggarwal, Varinder K.. "Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: Extensive studies to map out scope, limitations, and rationalization of diastereo- and enantioselectivities". supporting information. p. 11951 - 11966. Retrieved 2013/09/02.
• 2、 Lupton, David W,Taylor, Dennis K. "New mechanistic aspects on the catalytic transformation of vinylthiiranes to mono and disubstituted 3,6-dihydro-1,2-dithiins by tungsten pentacarbonyl monoacetonitrile". . p. 4517 - 4527. Retrieved 2007/10/03.