(3R)-2,3-diphenyloxirane

Base Information

• Chemical Name: (3R)-2,3-diphenyloxirane
• CAS No.: 1439-07-2
• Molecular Formula: C14H12O
• Molecular Weight: 196.249
• Hs Code.: 29109000
• European Community (EC) Number: 215-877-7
• Nikkaji Number: J1.170.204J
• Mol file: 1439-07-2.mol

Synonyms:stilbene oxide;stilbene oxide, (2R-trans)-isomer;stilbene oxide, (2S-trans)-isomer;stilbene oxide, (cis)-isomer;stilbene oxide, (trans)-isomer;stilbene oxide, trans-;stilbene oxide, trans-(+-)-isomer;trans-stilbene oxide

Chemical Property of (3R)-2,3-diphenyloxirane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00157mmHg at 25°C
• Melting Point: 65-67 °C(lit.)
• Refractive Index: 1.608
• Boiling Point: 304.5 °C at 760 mmHg
• Flash Point: 133.4 °C
• PSA: 12.53000
• Density: 1.136 g/cm³
• LogP: 3.49920
• Storage Temp.: 2-8°C
• Solubility.: soluble in Toluene
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 196.088815002
• Heavy Atom Count: 15
• Complexity: 179

Purity/Quality:

97% ^*data from raw suppliers

trans-Stilbene Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]2C(O2)C3=CC=CC=C3
• Uses: trans-Stilbene Oxide is used in preparation method of metal complex covalent organic framework material.

Technology Process of (3R)-2,3-diphenyloxirane

There total 439 articles about (3R)-2,3-diphenyloxirane 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: 92.0%

(E)-1,2-diphenyl-ethene (103-30-0) → benzaldehyde (100-52-7) + trans-Stilbene oxide (1439-07-2)

Guidance literature:

With [bis(acetoxy)iodo]benzene; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate); In dichloromethane; for 72h; Ambient temperature;

DOI:10.1039/a705109c

Reference yield: 79.0%

(E)-1,2-diphenyl-ethene (103-30-0) → 2,3-diphenyloxirane (1689-71-0,17619-97-5,25144-18-7,38628-70-5,40102-60-1,1439-07-2) + benzaldehyde (100-52-7)

Guidance literature:

With C₂₀H₂₄CoN₂O₆⁽¹⁺⁾*NO₃^(1-)*H₂O; oxygen; isobutyraldehyde; In acetonitrile; at 60 ℃; for 8h; under 760.051 Torr; Time;

DOI:10.1016/j.poly.2013.03.050

Reference yield: 76.0%

(E)-1,2-diphenyl-ethene (103-30-0) → benzaldehyde (100-52-7) + (R,R)-trans-stilbene epoxide (1439-07-2)

Guidance literature:

With iodosylbenzene; copper(II) nitrate; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/ja00315a071

upstream raw materials:

cis-stilben

(E)-1,2-diphenyl-ethene

(+)-2-<(S)-N-(α-methylbenzyl)-N-benzylsulfamyl>-3-(pentafluorophenyl)oxaziridine

(1S,2R)-1,2-diphenylethane-1,2-diol

Downstream raw materials:

N-(3-hydroxy-4-methoxybenzyl)-N-methyl-β-hydroxy-α-phenylphenethylamine

Diphenylacetaldehyde

(E)-1,2-diphenyl-ethene

(1R,2S)-2-azido-1,2-diphenylethan-1-ol

Refernces

Scandium-bipyridine-catalyzed, enantioselective alcoholysis of meso-epoxides

10.1002/ejoc.200601101

The study presents an investigation into the scandium-bipyridine-catalyzed enantioselective ring-opening of meso-epoxides using aliphatic alcohols. The research focuses on optimizing the reaction conditions to achieve high yields and enantioselectivities for the production of valuable 1,2-diol monoethers. The study evaluates various metal triflates, solvents, temperatures, ligand architectures, and catalyst loadings to enhance the catalytic efficiency. It was found that scandium-bipyridine complexes, particularly Sc(OTf)3 with bipyridine ligand 2, were the most effective catalysts, providing the best combination of activity and selectivity. The research also explores the scope and limitations of the reaction with different epoxides and alcohols, as well as the potential for catalyst loading reduction without compromising yield or enantioselectivity. A strong positive non-linear effect was observed, indicating aggregation phenomena of the chiral catalyst, which was further supported by structural insights from X-ray crystallography and ESI-MS spectra. The study contributes to the field by providing a method for the enantioselective synthesis of 1,2-diol monoethers from meso-epoxides and aliphatic alcohols.