2243-35-8

Usage

Uses

Used in Pharmaceutical Industry:
Phenacyl acetate is used as a key intermediate in the synthesis of enol phosphates, which are important compounds in the pharmaceutical industry. These enol phosphates have potential applications in the development of new drugs and therapeutic agents.
Used in Antifungal Agents:
Phenacyl acetate is also used in the preparation of triazole antifungals, such as (-)-Genazonazole. These antifungal agents are effective in treating various fungal infections and are widely used in the medical field.

InChI:InChI=1/C9H16O6/c1-7(12)14-5-9(3-10,4-11)6-15-8(2)13/h10-11H,3-6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 100874-10-0 2-bromo-1-phenyl-3-[2]pyridyl-propane-1,3-dione 
• 127-08-2 potassium acetate 
• 18735-16-5 α,β-diacetoxy-styrene 
• 108-24-7 acetic anhydride 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 
• 127-09-3 sodium acetate 
• 70-11-1 α-bromoacetophenone 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 64-17-5 ethanol 
• 54226-26-5 2-methyl-2-phenyl-1,3-benzoxathione 

Downstream Products

• 100-41-4 ethylbenzene 
• 103-45-7 acetic acid phenethyl ester 
• 861596-29-4 2,2-dimethyl-4-oxo-3-phenyl-butyric acid 
• 99155-28-9 2-oxo-4-phenyl-oxazolidine-4-carboxylic acid amide 
• 1575-47-9 4-phenyl-5H-furan-2-one 
• 25070-24-0 α-hydroxyacetophenone oxime 
• 20662-90-2 2-methyl-4-phenyloxazole 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 94574-75-1 3-hydroxy-2-phenyl-quinoline-4,6-dicarboxylic acid 
• 3319-03-7 2-dimethylamino-1-phenyl-ethanone 
• 15212-17-6 2.4-Dinitro-phenylhydrazon des ω-Acetoxy-acetophenons 
• 72335-13-8 (E)-Ethyl 4-Acetoxy-3-phenylbut-2-enecarboxylate 
• 72335-15-0 (Z)-Ethyl 4-Acetoxy-3-phenylbut-2-enecarboxylate 
• 93503-12-9 4-acetoxy-3-phenylbutanoic acid ethyl ester 

Relevant academic research and scientific papers

Calcium Complexation by α-Hydroxy Ketones. Characterization of a Calcium Complex of Phenacyl Alcohol

Solution and solid-state structural data are presented for a discrete complex of phenacyl alcohol with calcium chloride, (2+)*2Cl(-)*H2O, in which phenacyl alcohol serves as a bidentate ligand, with coordination of calcium to both the carbonyl oxygen and the hydroxyl group.This constitutes the first structural characterization of a calcium complex with the important pharmacophoric α-hydroxy ketone functionality.

Mechanistic Insights into the Formation of δ-Lactones by Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates

δ-Valerolactone derivatives are formed by the cerium-catalyzed, aerobic coupling of β-oxoesters with enol acetates and dioxygen. The products possess a 1,4-diketone moiety, thus, the conversion can be regarded as an Umpolung since the β-oxoesters are oxidized to electrophilic α-radicals. The transformation has similarities to the Baeyer-Villiger oxidation (BVO) where the higher substituted residue migrates. An endoperoxidic oxycarbenium ion comparable to the Criegee intermediate in the BVO is proposed as a reaction intermediate in this case of the oxidative C?C coupling reaction, but in contrast to the BVO, the less substituted alkyl residue migrates. It was demonstrated by the conversion of β-oxoesters with two stereocenters that this 1,2-alkyl shift proceeds with retention of configuration. A radical chain mechanism of the coupling reaction was furthermore evidenced by the conversion of enol acetates and β-oxoesters with cyclopropyl substituents. Isolation and characterization of products with opened cyclopropane rings established the constitution of radical intermediates.

The ortho-Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Presented herein is an intriguing effect of fluorine, and it allows difluoroenol silyl ethers to couple with aryliodanes in a redox-neutral manner to afford ortho-iodo difluoroalkylated arenes. The remaining iodide group provides a versatile platform for converting the products into various valuable difluoroalkylated arenes. The reaction shows excellent functional-group compatibility and broad substrate scope. A DFT mechanistic study suggests that the fluorine effect facilitates a subtle nucleophilic attack of the oxygen atom of enol silyl ethers onto aryliodanes, therefore leading to a rearrangement.

A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from α-oxy-substituted derivatives through no

The photooxidation of 2′-deoxyguanosine (dG) and its derivative 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) by a series of acetophenones (AP-X) and benzophenone (BP) has been studied. The favorable absorption characteristics of the benzoyl chromophore e

Iron-catalyzed ketonization of 2-aryl-1,1-dibromoalkenes with KOAc: Synthesis of α-acetoxy aryl ketones via a Michael-like addition process

A novel and convenient iron-catalyzed ketonization of 2-aryl-1,1- dibromoalkenes with KOAc has been achieved. A series of α-acetoxy aryl ketones were prepared with moderate yields via 2-carbon position functionalization of 2-aryl-1,1-dibromoalkenes.

Conjugate Addition of Acyloxy Groups to Alkynylphenyliodonium Tetrafluoroborates under Both Basic and Acidic Conditions. Synthesis of α-Acyloxy Ketones

Reaction of alkynylphenyliodonium tetrafluoroborates 1 with sodium salts of carboxylic acids in the presence of water affords α-acyloxy ketones.The reaction also proceeds under acidic conditions.The fact that the reaction of (4-hydroxy-1-butynyl)phenyliod

Study on the reactive transient α-λ3-iodanyl- acetophenone complex in the iodine(III)/PhI(I) catalytic cycle of iodobenzene-catalyzed α-acetoxylation reaction of acetophenone by electrospray ionization tandem mass spectrometry

RATIONALE Hypervalent iodine compounds are important and widely used oxidants in organic chemistry. In 2005, Ochiai reported the PhI-catalyzed α-acetoxylation reaction of acetophenone by the oxidation of PhI with m-chloroperbenzoic acid (m-CPBA) in acetic acid. However, until now, the most critical reactive α-λ3-iodine alkyl acetophenone intermediate (3) had not been isolated or directly detected. METHODS Electrospray ionization tandem mass spectrometry (ESI-MS/MS) was used to intercept and characterize the transient reactive α-λ3- iodine alkyl acetophenone intermediate in the reaction solution. RESULTS The trivalent iodine species was detected when PhI and m-CPBA in acetic acid were mixed, which indicated the facile oxidation of a catalytic amount of PhI(I) to the iodine(III) species by m-CPBA. Most importantly, 3·H+ was observed at m/z 383 from the reaction solution and this ion gave the protonated α-acetoxylation product 4·H+ at m/z 179 in MS/MS by an intramolecular reductive elimination of PhI. CONCLUSIONS These ESI-MS/MS studies showed the existence of the reactive α-λ3-iodine alkyl acetophenone intermediate 3 in the catalytic cycle. Moreover, the gas-phase reactivity of 3·H+ was consistent with the proposed solution-phase reactivity of the α-λ3-iodine alkyl acetophenone intermediate 3, thus confirming the reaction mechanism proposed by Ochiai. Copyright

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones

Novel decarboxylative oxyacyloxylation of propiolic acids has been developed. This reaction provides an efficient access to alkynyl-containing α-acyloxy ketones from readily available starting materials and exhibits significant functional group tolerance. Furthermore, oxyacyloxylation of terminal alkynes and aliphatic propiolic acids was also developed. A possible reaction mechanism is proposed based on mechanistic studies.