60843-66-5

Usage

Uses

Used in Pharmaceutical Production:
2,2-dimethyl-1-(3-phenyloxiran-2-yl)propan-1-one is used as a synthetic intermediate for the production of pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of various drugs, contributing to the development of new medications.
Used in Organic Chemistry:
2,2-dimethyl-1-(3-phenyloxiran-2-yl)propan-1-one is used as a synthetic intermediate in organic chemistry. Its versatile structure makes it a valuable compound for the synthesis of a wide range of organic compounds, facilitating research and development in the field.
Used in Material Science:
2,2-dimethyl-1-(3-phenyloxiran-2-yl)propan-1-one may have potential applications in the development of new materials. Its unique structure could be utilized in the creation of novel materials with specific properties, such as improved strength, flexibility, or chemical resistance.
Used in Bioactive Compound Development:
2,2-dimethyl-1-(3-phenyloxiran-2-yl)propan-1-one may also exhibit potential applications in the development of bioactive compounds. Its chemical properties could be harnessed to create new compounds with biological activity, potentially leading to advancements in medicine and biotechnology.

Upstream product

• 594-19-4 tert.-butyl lithium 
• 119163-37-0 ((2S,3R)-3-Phenyl-oxiranyl)-pyrrolidin-1-yl-methanone 
• 538-44-3 (E)-benzylidenepinacolone 
• 115505-36-7 (3,3-dimethyl-1-butynyl)(phenyl)(tetrafluoroborato)-λ³-iodane 
• 100-52-7 benzaldehyde 
• 5469-26-1 1-Bromopinacolon 
• 1351657-47-0 (E)-2-phenylacetaldehyde O-4,4-dimethyl-1-phenylpent-2-ynyl oxime 
• 1228682-72-1 C₁₃H₁₇NO 
• 19202-21-2 1-trans-cinnamoylpyrrolidine 
• 538-44-3 4,4-dimethyl-1-phenyl-1-penten-3-one 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 30263-65-1 1,1-dibromo-3,3-dimethylbutan-2-one 

Downstream Products

• 855381-19-0 2-hydroxy-4,4-dimethyl-1-phenyl-pentan-3-one 
• 7042-30-0 (2R,3S)-3-phenyloxirane-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis

A simple asymmetric epoxidation method is developed to effectively synthesize chiral α-carbonyl epoxides through an amine-thiourea dual activation catalysis. In this method, TBHP, as an oxidant, determined the reaction rate, and the chiral amine-thiourea catalyst effectively controlled the stereoselectivity of the reaction, and KOH promoted deprotonation. 22 examples of α,β-unsaturated ketones with various substituent groups are smoothly converted into α-carbonyl epoxides with moderate to excellent enantiomeric excess.

Method for preparing epoxide by one-pot olefin aerobic epoxidation

The invention relates to a method for preparing an epoxide by one-pot olefin aerobic epoxidation, and belongs to the technical field of organic synthesis. An olefin, an alkyl aromatic compound and analkali are added into a solvent, or an olefin, an alkyl aromatic compound and an alkali are directly mixed; the temperature is raised to 70-160 DEG C in an air or oxygen atmosphere; reacting is carried out for 1-48 hours; and the olefin is directly oxidized into the corresponding epoxide in the presence of the alkyl aromatic compound, the alkali and air (or oxygen), wherein the yield is up to 99%.In the reaction process, the generated alkyl peroxide is generated in situ and consumed in situ, so that the concentration of the alkyl peroxide is kept at a lower level; and generated alkyl peroxy free radicals can also react with the olefin to further generate the peroxide, and efficiency is improved. The method has the advantages of simple operation, mild conditions, low raw material cost andno need of special complex equipment, and has a good industrial application prospect.

Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.

Copper-catalyzed skeletal rearrangement of O-propargylic alkylaldoximes via N-O bond cleavage

O-Propargylic oximes that possess a proton at the α-position of the oxime group were effectively converted to the corresponding oxiranyl N-alkenylimines via a 5-endo-dig cyclization followed by the cleavage of the N-O bond.

Generation and reaction of monocarbonyliodonium ylides: Ester exchange of (Z)-(β-acetoxyvinyl)iodonium salts with lithium ethoxide and synthesis of α,β-epoxy ketones

Reported here for the first time are the generation of monocarbonyliodonium ylides and their alkylidene-transfer reactions to aldehydes yielding α,β-epoxy ketones. Exposure of (Z)-(2-acetoxy-1-decenyl)iodonium bromide, prepared stereoselectively by sodium acetate-catalyzed Michael addition of acetic acid to (1-decynyl)(phenyl)iodonium salt, to EtOLi in THF at -78°C results in ester exchange to generate the monocarbonyliodonium ylide with the liberation of ethyl acetate. 1H NMR measurements indicate that the ylide is stable up to -30°C in THF-d8 but gradually decomposes at -20°C to 1-bromo-2-decanone. The monocarbonyliodonium ylide acts as an alkylidene-transfer agent to carbonyl compounds, and the reaction with aldehydes in THF-DMSO at -30°C gives α,β-epoxy ketones with E-isomers as a major product. With an α,β-unsaturated aldehyde, selective 1,2-addition to the carbonyl group was observed. The relative rates of the alkylidene-transfer reaction of this ylide for a series of ring-substituted benzaldehydes were measured. A Hammett correlation plot with the σ constants of substituents afforded the reaction constant ρ = 2.95 (r = 1.00), which indicates that the monocarbonyliodonium ylide is moderately nucleophilic in nature.

Development of the Julia asymmetric epoxidation reaction. Part 1. Application of the oxidation to enones other than chalcones

Asymmetric epoxidation of a variety of enones 3, 6, 8, 10, 12, 14, 16, 18, 21, 22, 26, 28-30 and 36 gives the corresponding oxiranes in good to excellent yield and optical purity. The oxidation medium consists of basic peroxide or sodium perborate or sodi

Development of the Julia asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters

Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4, 9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 ± 10 leucine residues.

Triphenylbismuthonium 2-Oxoalkylide, A Moderately Stabilized Bismuthonium Ylide: Generation and Reactions with Some Electrophiles

Treatment of (2-oxoalkyl)triphenylbismuthonium tetrafluoroborates 3 with potassium tert-butoxide in tetrahydrofuran at -78 deg C produced triphenylbismuthonium 2-oxoalkylides 4, which readily underwent epoxidation with the aldehydes 5 to give the α,β-epoxy ketones 7 with highly trans selectivity.The ylide 4a reacted with dimedone 11, the sulfonic acid 13, the thiol 15 and the isocyanate 17 to afford the corresponding ketones 12, 14, 16 and 19 in moderate to good yields.Reaction of the ylide 4c with the α,β-unsaturated ketones 10 and 21 afforded the 1,2-dibenzoyl- and the 1,2,3-tribenzoyl- cyclopropanes 20 and 22, respectively, although the yields were low.In the presence of a catalytic amount of nitrosobenzene 23, the ylide 4a a unique decomposition to give the 2,2,7,7-tetramethyloct-4-ene-3,6-dione 24 in quantitative yield, while the reaction with the nitrile oxide 25 yielded the isoxazoline 26.In all of these reactions, triphenylbusmuthane 6 was the additional major product.

A Novel Darzens-Type Reaction Promoted by Tributylstannylcarbamate

Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from α-halo ketones.Thus, a Darzens reaction was achieved under mild and neutral conditions.The reaction took place without any side reactions and even with aliphatic α-halo ketones bearing enolizable α'-hydrogens.Various types of α,β-epoxy ketones and esters were obtained in this one-pot reaction.The stereoselectivity of the reaction was influenced by changing the halogen substituent of the α-halo ketones and by additives.Moreover, the present method could be appliedto γ- and δ-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.

REACTIONS OF POLYHALO FUNCTIONAL COMPOUNDS WITH METALS AND ELECTROPHILIC REAGENTS. XVI. CHEMICAL BEHAVIOR OF α,α-DIBROMO KETONES IN THE REFORMATSKII REACTION

Geminal α,α-dibromo ketones react with zinc and carbonyl compounds.Depending on the structures of the reactants, the nature of the solvent, and the reaction conditions, α,β-unsaturated ketones, α,β-epoxy ketones, or α-alkyl-β-diketones or their mixtures are formed.