17257-79-3

Usage

Uses

Used in Pharmaceutical Industry:
2β-Acetyl-3α-methyloxirane is used as a starting material for the synthesis of chiral peroxides, which are biologically interesting and may hold clinical importance. These chiral peroxides can be utilized in the development of new drugs and therapeutic agents, contributing to advancements in medicine.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2β-Acetyl-3α-methyloxirane serves as a valuable intermediate for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and functional group transformations, making it a versatile building block in organic chemistry.
Used in Research and Development:
2β-Acetyl-3α-methyloxirane is also used in research and development for studying the properties and reactivity of oxirane-containing compounds. Its synthesis and application in various chemical reactions can provide insights into the behavior of similar molecules, furthering our understanding of organic chemistry and its applications.

InChI:InChI=1/C5H8O2/c1-3(6)5-4(2)7-5/h4-5H,1-2H3

Upstream product

• 625-33-2 3-penten-2-one 
• 3102-32-7 (Z)-3-penten-2-one 
• 3102-33-8 trans-3-penten-2-one 
• 75-91-2 tert.-butylhydroperoxide 
• 80-15-9 Cumene hydroperoxide 
• 88339-92-8 C₁₁H₂₀HgO₅ 
• 103144-67-8 trans-3-methyl-2-acetyloxirane diethylketal 

Downstream Products

• 100061-91-4 3,4-epoxy-pentan-2-one-(2,4-dinitro-phenylhydrazone) 
• 101420-60-4 3,4-dihydroxy-pentan-2-one 
• 67-56-1 methanol 
• 702651-39-6 (E)-3-Dimethylamino-1-(3-methyl-oxiranyl)-propenone 
• 600-14-6 2,3-Pentanedione 
• 123-54-6 acetylacetone 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 105827-07-4 C₂₉H₃₉Cl₃O₉ 
• 71808-93-0 (Z)-3-Thiocyanato-pent-3-en-2-one 
• 3102-33-8 trans-3-penten-2-one 
• 83750-10-1 1-((4R,5R)-2,4-Dimethyl-4,5-dihydro-oxazol-5-yl)-ethanone 
• 103144-77-0 trans-3-methyl-2-acetylthiirane 

Relevant academic research and scientific papers

Iron-Catalyzed Epoxidation of Linear α-Olefins with Hydrogen Peroxide

The combination of Fe(OTf)2 with N-methyl bis(picolylamine) (Me-bpa) L7 enables epoxidation of linear olefins including terminal, internal, and cyclic ones, using hydrogen peroxide as terminal oxidant under mild conditions. In the presence of picolinic acid as additive improved yields of epoxides up to 75 % have been achieved.

Catalytic enantioselective peroxidation of α,β-unsaturated ketones

Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available α,β-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established. Copyright

Facile epoxidation of α,β-unsaturated ketones with cyclohexylidenebishydroperoxide

Cyclohexylidenebishydroperoxide was successfully used as the oxygen source for the oxidation of α,β-unsaturated ketones for the first time. The corresponding epoxides were obtained in excellent yields under the Weitz-Scheffer reaction conditions.

Ultrasound-assisted epoxidation of olefins and α,β-unsaturated ketones over hydrotalcites using hydrogen peroxide

An efficient ultrasound-assisted epoxidation of olefins and α,βunsaturated ketones over hydrotalcite catalysts in the presence of hydrogen peroxide and acetonitrile is described. This general and selective protocol is relatively fast and is applicable to a wide variety of substrates.

TRANSFORMATION OF ACETYLOXIRANES TO THIIRANE ANALOGS

A method for the synthesis of acetylthiiranes was developed; this method includes the conversion of acetyloxiranes to diethylketals, dealkoxylation of the latter, replacement of the oxygen atom of the oxirane ring by sulfur, and acidic hydrolysis of the ethoxyvinylthiirane to acetylthiiranes.

FORMATION OF α,β-EPOXY SYSTEMS FROM β-PEROXY CARBON FREE RADICALS

The conversion of β-peroxy carbon free radicals to α,β-epoxides is a facile process of broad scope and may be a key step in the biosynthesis of clavulones.

Reaction of Epoxides with Triphenylphosphine-Thiocyanogen (TPPT): Preparation of α-Thiocyanatovinyl Ketones, vis-Dithiocyanates, and vic-Dithiocyanatohydrins

A number of epoxides smoothly react with TPPT under mild conditions to give α-thiocyanatovinyl ketones, vic-dithiocyanates, or vic-thiocyanatohydrins, depending on the structures of the epoxides used.The reactions proceed site- and stereo-specifically, to give α-thiocyanatovinyl ketones from αβ-epoxyketones, threo-dithiocyanate from trans-epoxide, erythro-dithiocyanate from cis-epoxide, and vic-thiocyanatohydrins from 1,1-disubstituted or fused epoxides, respectively.A possible mechanism for these reactions is put forward.

Kinetics of Epoxidation of α,β-Unsaturated Ketones in Methanol Medium

The kinetics of epoxidation of α,β-unsaturated ketones by alkaline H2O2 in methanol in the temperature range 25-40 deg C has been studied.The addition follows second order kinetics.The results indicate that the concentration of NaOH has a significant effect on the reactivity.The effect of various substituents in these reactions show that electron-releasing groups attached to the β-carbon atom in the olefin diminish the rate and electron-attracting groups enhance it.The oxidative cleavage of a few substituted epoxychalkones by hydroperoxide anion has also been studied in methanol at 30 deg C.Adherence to second order kinetics is excellent in every case and the rates are slower than those of the corresponding chalkones.The stability of epoxides depends on the substituents; electron-releasing groups diminish the rate and electron-attracting groups enhance it as observed in the case of epoxidation.The reaction obeys the Arrhenius equation and the respective activation parameters have been calculated.The effect of solvent polarity on the rate of epoxidation has been studied.The differences in the rates in methanol and water as solvents have been explained on the basis of solvent-solute interaction.

A STEREOSELECTIVE REDUCTION OF α,β-EPOXY KETONES WITH DIBORANE AND 9-BORABICYCLONONANE

The stereochemical course of reduction of α,β-epoxycyclohexanones and aliphatic α,β-epoxy ketones with diborane and 9-borabicyclononane is described.Diastereomeric epoxy alcohols are formed in good yields and in some cases with high selectivity.It has been found that 9-borabicyclononane shows higher stereoselectivity than diborane in the reduction of α,β-epoxy ketones.

SYNTHESIS OF 2-ALKYLTHIO-5-ACETYL-2-OXAZOLINES

The reaction of 2-acetyloxiranes with alkyl thiocyanates in the presence of Lewis acids (BF3, AlCl3) has given 2-alkylthio-5-acetyl-2-oxazolines (yields 40-60percent).It has been shown that the reaction of trans-2-acetyl-3-methyloxirane and of trans-2-acetyl-3-methyloxirane and of trans-2-acetyl-2,3-dimethyloxirane with alkyl thiocyanates takes place stereospecifically and leads to cis-2-alkylthio-5-acetyl-2-oxazolines.