182486-10-8

Basic information

• Product Name: Oxirane, 2-methyl-2-[(1E)-2-phenylethenyl]-
• CAS NO: 182486-10-8
• Molecular Formula: C11H12O
• Molecular Weight: 160.216
• Mol File: 182486-10-8.mol

Chemical Properties

• CAS DataBase Reference: Oxirane, 2-methyl-2-[(1E)-2-phenylethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, 2-methyl-2-[(1E)-2-phenylethenyl]-(182486-10-8)
• EPA Substance Registry System: Oxirane, 2-methyl-2-[(1E)-2-phenylethenyl]-(182486-10-8)

Safety Data

• Hazardous Substances Data: 182486-10-8(Hazardous Substances Data)

Upstream product

• 122-57-6 1-Phenylbut-1-en-3-one 
• 74-95-3 1,1-dibromomethane 
• 2181-42-2 trimethylsulphonium iodide 
• 1896-62-4 (E)-benzalacetone 
• 2181-44-4 trimethylsulfonium methylsulfate 

Downstream Products

• 1896-62-4 (E)-benzalacetone 
• 79238-23-6 (3E)-2,2-dimethyl-4-phenyl-3-butenal 
• 221557-38-6 (E)-2-methyl-4-phenylbut-3-en-1-ol 
• 175793-19-8 (3E)-2-methyl-4-phenylbutenal 

Relevant articles and documents

Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium

A scalable procedure for the direct preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including α-chloroketones, which typically fail under classic Corey-Chaykovsky conditions. This advantage has been used to develop a novel route toward the drug fluconazole.

Retro-Corey-Chaykovsky Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones

Corey-Chaykovsky epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an alternative strategy of the acid-catalyzed Meinwald rearrangement or oxidation for conversion of epoxides to carbonyl compounds.

Chemoselective cross metathesis of bishomoallylic alcohols: Rapid access to fragment A of the cryptophycins

Equation presented. The racemic or enantioselective allylation of in situ formed β,γ-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross

Enantioselective allylation of β,γ-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes

(matrix presented) 2-Vinyloxiranes have been found to be excellent surrogates to β,γ-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)3, are effectively tr

Total synthesis of cryptophycins via a chemoenzymatic approach

A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

TRIMETHYLSULFONIUM METHYLSULFATE, A SIMPLE AND EFFICIENT EPOXIDIZING AGENT.

Sulfonium salts 1 and 3 are highly reactive epoxidizing agents under phase transfer catalytic conditions.