1,3-Diphenyl-2,3-epoxy-1-propanone

Base Information

• Chemical Name: 1,3-Diphenyl-2,3-epoxy-1-propanone
• CAS No.: 5411-12-1
• Molecular Formula: C15H12 O2
• Molecular Weight: 224.259
• Hs Code.: 2914399090
• European Community (EC) Number: 226-487-1
• NSC Number: 402160,10919
• DSSTox Substance ID: DTXSID40968993
• Nikkaji Number: J217.980F
• Pharos Ligand ID: 4QAS9GBQLHTT
• ChEMBL ID: CHEMBL1733373
• Mol file: 5411-12-1.mol

Synonyms:chalcone epoxide;chalcone epoxide, (2R)-(trans)-isomer;chalcone epoxide, (cis)-(-)-isomer;chalcone epoxide, (cis)-isomer;chalcone epoxide, (trans)-isomer;chalcone oxide;trans-1-benzoyl-2-phenyloxirane

Chemical Property of 1,3-Diphenyl-2,3-epoxy-1-propanone

Chemical Property:

• Vapor Pressure: 8.53E-06mmHg at 25°C
• Melting Point: 88-90°C
• Boiling Point: 374.1°Cat760mmHg
• Flash Point: 174°C
• PSA: 29.60000
• Density: 1.209g/cm³
• LogP: 3.00940
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenyl-(3-phenyloxiran-2-yl)methanone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)C(=O)C3=CC=CC=C3

Technology Process of 1,3-Diphenyl-2,3-epoxy-1-propanone

There total 147 articles about 1,3-Diphenyl-2,3-epoxy-1-propanone 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: 100.0%

benzalacetophenone (94-41-7) → chalcone epoxide (5411-12-1)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In dimethyl sulfoxide; at 60 ℃; for 1h; Solvent;

DOI:10.1021/acs.joc.7b01679

Reference yield: 100.0%

1,3-diphenyl-propen-3-one (614-47-1) → chalcone epoxide (5411-12-1)

Guidance literature:

With tert.-butylhydroperoxide; aluminum oxide; potassium fluoride; In 1,2-dichloro-ethane; acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1016/0040-4020(95)01026-2

Reference yield: 94.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + benzaldehyde (100-52-7) → chalcone epoxide (5411-12-1)

Guidance literature:

With tert.-butylhydroperoxide; In water; acetonitrile; at 90 ℃; for 10h; Reagent/catalyst; Schlenk technique;

DOI:10.1002/cctc.201402839

upstream raw materials:

1,3-diphenyl-propen-3-one

cis-2,3-epoxy-1,3-diphenylpropan-1-ol

benzaldehyde

1,3-diphenyl-1-propyn-3-ol

Downstream raw materials:

(2RS,3SR)-2,3-epoxy-1,1,3-triphenyl-propan-1-ol

2-hydroxy-3-methoxy-1,3-diphenylpropan-1-one

1,3-diphenylpropane-1,2-dione

erythro-N-(2-benzoyl-1-phenyl-2-chloroethyl)-S-methyl thiocarbamate

Refernces

ENANTIOSELECTIVE SYNTHESIS OF FLAVONOIDS. PART 1. POLY-OXYGENATED CHALCONE EPOXIDES

10.1016/S0040-4020(01)82043-3

The research focuses on the enantioselective synthesis of poly-oxygenated chalcone epoxides, which are potentially useful as chiral precursors for the synthesis of enantiomerically enriched dihydroflavonols. The study employs the epoxidation of various poly-oxygenated chalcones using hydrogen peroxide (H2O2) in the presence of poly-α-amino acid catalysts. The resulting chiral aromatic oxygenated epoxides were characterized by their optical yields and absolute configurations, which were determined using circular dichroism (CD) spectroscopy. The research found that the oxygen functionalities and the position of substituents on the chalcone structure significantly influence the stereochemistry of the reaction. However, the study also encountered challenges such as low chemical yields and decreased optical purity during the conversion of the epoxides to dihydroflavonols, indicating that further optimization is needed to enhance the practicality of this synthetic approach for the production of C-4-oxygenated flavonoids.