1817-57-8

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenyl-3-butyn-2-one is used as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the development of new pharmaceuticals.
In the synthesis of pharmaceuticals, 4-Phenyl-3-butyn-2-one can undergo various reactions, such as bromination, iodination, and reduction, to form different derivatives with potential therapeutic applications. These reactions can be carried out in different solvents, such as CH2Cl2, CH2Cl2/pyridine, and MeOH, to optimize the reaction conditions and yield.
Overall, 4-Phenyl-3-butyn-2-one plays a crucial role in the pharmaceutical industry as a versatile intermediate for the development of new drugs and therapeutic agents. Its unique chemical properties and reactivity make it an essential component in the synthesis of a wide range of pharmaceutical compounds.

Synthesis Reference(s)

Chemistry Letters, 9, p. 1327, 1980The Journal of Organic Chemistry, 47, p. 2549, 1982 DOI: 10.1021/jo00134a010Tetrahedron Letters, 29, p. 2321, 1988 DOI: 10.1016/S0040-4039(00)86048-7

InChI:InChI=1/C10H8O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,1H3

Upstream product

• 506-96-7 Acetyl bromide 
• 1004-22-4 (phenylethynyl)sodium 
• 108-24-7 acetic anhydride 
• 60-29-7 diethyl ether 
• 75-36-5 acetyl chloride 
• 141-78-6 ethyl acetate 
• 536-74-3 phenylacetylene 
• 127-19-5 N,N-dimethyl acetamide 
• 6077-10-7 bis(phenylethynyl)mercury 
• 30665-96-4 2-phenylethynyl phenyl selenide 
• 540-88-5 acetic acid tert-butyl ester 
• 105-46-4 sec-Butyl acetate 
• 93-91-4 1-phenylbutan-1,3-dione 
• 618-42-8 1-piperidin-1-yl-ethanone 

Downstream Products

• 93-91-4 1-phenylbutan-1,3-dione 
• 2832-97-5 4-(4-morpholyl)-2-phenylthiophene 
• 18940-23-3 1-(1-morpholino)-1-phenyl-1-buten-3-one 
• 3729-90-6 3-methyl-1,5-diphenyl-1H-pyrazole 
• 10250-60-9 1,5-dimethyl-3-phenyl-1H-pyrazole 
• 10250-58-5 1,3-dimethyl-5-phenyl-1H-pyrazole 
• 56215-31-7 2-(5-acetyl-2-oxo-4-phenyl-2,3-dihydro-furan-3-yl)-1-methyl-pyridinium betaine 
• 20964-92-5 1-Diaethylamino-1-phenyl-buten-⁽¹⁾-on-⁽³⁾ 
• 70871-79-3 E-1-morpholino-1-phenyl-1-buten-3-one 
• 70871-78-2 Z-1-morpholino-1-phenyl-1-buten-3-one 
• 71127-25-8 (Z)-4-Imidazol-1-yl-4-phenyl-but-3-en-2-one 
• 71127-26-9 (E)-4-Imidazol-1-yl-4-phenyl-but-3-en-2-one 
• 117390-21-3 (Z)-4-(1H-Benzoimidazol-2-ylmethylselanyl)-4-phenyl-but-3-en-2-one 
• 117390-22-4 (E)-4-(1H-Benzoimidazol-2-ylmethylselanyl)-4-phenyl-but-3-en-2-one 

Relevant academic research and scientific papers

Efficient large-scale synthesis of 4-phenyl-3-butyn-2-one, a key intermediate for a novel potent adenosine antagonist

Phenylacetylenic Grignard reagent reacts with acetic anhydride under mild conditions to give 4-phenyl-3-butyn-2-one in high yield. This method was applicable to a large-scale synthesis, and optimized reaction conditions have been investigated.

Mechanistic diversity of the selective oxidations mediated by supported iron phthalocyanine complexes

Selective oxidations of (i) phenols and condensed aromatics to quinones and (ii) alkynes to α,β-acetylenic ketones mediated by supported iron phthalocyanine complexes exhibit very different mechanistic features as evidenced by 18O labelling and kinetic isotope effect studies. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.

Stereo and regioselective synthesis of (Z)-β-arylseleno-α,β- unsaturated ketones via selenocarbonylation addition of arylselenoesters to alkynes catalyzed by copper(I)

Selenocarbonylation addition reaction of selenoesters to nonactived terminal alkynes under the catalysis of CuX products (Z)- β-arylseleno-α,β-unsaturated ketones in high selectivity and high yields. The mechanism of this reaction is also discussed.

Preparation of α,β-acetylenic ketones by catalytic heterogeneous oxidation of alkynes

Covalent grafting of iron phthalocyanines onto silica affords active catalysts for selective oxidation of alkynes and propargylic alcohols to α,β-acetylenic ketones, highly valuable precursors in the preparation of fine chemicals.

Oxaphospholes and bisphospholes from phosphinophosphonates and α,β-unsaturated ketones

The reaction of a {W(CO)5}-stabilized phosphinophosphonate 1, (CO)5WPH(Ph)-P(O)(OEt)2, with ethynyl- (2 a-f) and diethynylketones (7-11, 18, and 19) in the presence of lithium diisopropylamide (LDA) is examined. Lithiated

Propargylic C[sbnd]H activation using a Cu(II) 2-quinoxalinol salen catalyst and tert-butyl hydroperoxide

The oxidation of alkynes to α,β-acetylenic carbonyls was achieved using only 1 mol% of a Cu(II) 2-quinoxalinol salen catalyst with tert-butyl hydroperoxide. These reactions proceed under mild conditions (70 °C) with excellent selectivity, producing yields up to 78%, and were used on a variety of alkyne substrates to produce the desired corresponding α,β-acetylenic ketones. In addition, these reactions can be run under aqueous conditions using a sulfonated version of the 2-quinoxalinol salen with good yields, reducing the need for volatile organic solvents.

Synthesis of 2-phenylethynyl-1,3-dioxanes and their hydrolysis

2-Phenylethynyl substituted 1,3-dioxanes were obtained by the reaction of 1,3-dioxanium salts with an Iotsich reagent. It was shown that they are readily hydrolyzed with the formation of α-acetylenic ketones. A simple new method is proposed for the synthe

Fine-tuning dirhodium compounds with bridging ligands: Synthesis, structure, catalytic efficiency

The structure of dirhodium compounds contains a unique Rh-Rh bond, two axial ligands and four bridging ligands. In the dirhodium(II) compounds, it is easy to migrate the coordinating atoms of the bridging ligand during the catalysis process, which leads to the degradation of the catalyst. Coordination atom migration was identified in bridging ligands. To improve the catalyst stability, we carried out a study on the effect of fine-tuning of the bridging ligand on the dirhodium compound. Several dirhodium compounds were designed and synthesized. During this process, we have successfully found Rh2(5-Br-esp)2 and Rh2(5-tBu-esp)2, which are closer to the ideal geometric configuration of the dirhodium(II) compounds. Rh2(5-Br-esp)2 has been applied in the oxidation of propargyl position and Rh2(5-tBu-esp)2 in the formation reaction of the C–N bond.

Synthesis of Highly Substituted Biaryls by the Construction of a Benzene Ring via in Situ Formed Acetals

Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Br?nsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.

Base-Promoted Synthesis of Polysubstituted 4-Aminoquinolines from Ynones and 2-Aminobenzonitriles under Transition-Metal-Free Conditions

A transition-metal-free and base-promoted one-pot reaction of ynones with 2-aminobenzonitriles is described. The reaction was initiated through sequential aza-Michael addition/intramolecular annulation to afford various multisubstituted 4-aminoquinolines