Synthesis of 2-benzoyl-3-phenyloxirane

Preparation of 2-benzoyl-3-phenyloxirane

Preparation of 2-benzoyl-3-phenyloxirane

Preparation of 2-benzoyl-3-phenyloxirane

A solution of benzylidene acetophenone (chalcone) (2.08 g, 10mmoles) in methanol (25 ml) is treated with 15% hydrogen peroxide (3 ml, ca. 12mmoles) and 2N sodium hydroxide solution (2.5 ml), with cooling to keep the temperature at not more than 30°. After a short time the solution suddenly sets to a crystal paste. Suction and washing with a little methanol give colorless crystals (1.8 g); if treated with water the mother-liquor provides a further 0.2 g. Total yield, 89%; m.p. 90°C.

Ber. Deut. Chem. Ges., 54, 2327 (1921).

IUPAC Name

phenyl-(3-phenyloxiran-2-yl)methanone

InChI

InChI=1S/C15H12O2/c16-13(11-7-3-1-4-8-11)15-14(17-15)12-9-5-2-6-10-12/h1-10,14-15H

InChI Key

UQGMJZQVDNZRKT-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C2C(O2)C(=O)C3=CC=CC=C3

MeSH 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

Depositor-Supplied Synonyms

2-benzoyl-3-phenyloxirane, Chalcone oxide, 5411-12-1, 1,3-Diphenyl-2,3-epoxy-1-propanone, phenyl(3-phenyloxiran-2-yl)methanone, trans-Chalcone oxide, CCRIS 2214, CHALCONE alpha,beta-EPOXIDE, UQGMJZQVDNZRKT-UHFFFAOYSA-N, Methanone, phenyl(3-phenyloxiranyl)-, NSC 402160, phenyl-(3-phenyloxiran-2-yl)methanone, 7570-86-7, Chalcone trans-.alpha.,.beta.-epoxide, trans-Phenyl(3-phenyloxiranyl)methanone, Chalcone epoxide, Propiophenone, 2,3-epoxy-3-phenyl-, trans-, F3097-0430, AC1L3NO1, AC1Q1HF1, AC1Q5G2S, SCHEMBL657100, CHEMBL1733373, CTK2H9098, Chalcone-.alpha.,.beta.-epoxide, Phenyl (3-phenyloxiranyl) ketone, BDBM129323, KST-1B8643, phenyl 3-phenyloxiran-2-yl ketone, NSC10919, EINECS 226-487-1, AR-1B7164, MFCD00022336, NSC 10919, NSC-10919, NSC402160, STL360884, 1,3-Diphenyl-2-propen-1-one Oxide, AKOS001028857, AKOS016368884, phenyl (3-phenyloxiran-2-yl)methanone, MCULE-9647389059, NE26749, NSC-402160, VZ23818, Phenyl(3-phenyl-2-oxiranyl)methanone #, AK395444, HE003120, HE321873, HE386328, phenyl-(3-phenyl-oxiran-2-yl)-methanone, AI3-50389, DB-020552, KB-228361, KB-259243, LS-125235, D4378, ST50410623, US8815951, Epoxide Hydrolase Inhibitor 1, Methanone, phenyl(3-phenyloxiranyl)-, trans-, I14-23034, Methanone, phenyl(3-phenyloxiranyl)-, trans- (9CI), T0500-1683

Removed Synonyms

chalcone epoxide, (cis)-isomer, trans-1-benzoyl-2-phenyloxirane, chalcone epoxide, (trans)-isomer, MolPort-000-659-724, CID92219, chalcone epoxide, (cis)-(-)-isomer, chalcone epoxide, (2R)-(trans)-isomer, trans-1,3-Diphenyl-2,3-epoxypropan-1-one, Methanone, phenyl[(2R,3R)-3-phenyloxiranyl]-, C028770, 79700-61-1

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