768-03-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-2-propen-1-one is used as a chemical reagent for the synthesis of pharmaceutical agents. It plays a crucial role in the preparation of various therapeutic compounds, such as functionalized aminoindolizines and pyrano[3,2-x]coumarins. These compounds have potential applications in the development of new drugs for the treatment of various diseases and conditions.
Used in Chemical Synthesis:
1-Phenyl-2-propen-1-one is also used as an intermediate in the synthesis of other organic compounds, such as dyes, perfumes, and flavorings. Its reactivity and versatility make it a valuable building block in the chemical industry for creating a wide range of products with diverse applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1602, 1973 DOI: 10.1021/jo00948a033Synthetic Communications, 23, p. 543, 1993 DOI: 10.1080/00397919308009811

Safety Profile

A poison by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

InChI:InChI=1/C9H8O/c1-2-9(10)8-6-4-3-5-7-8/h2-7H,1H2

Upstream product

• 75-15-0 carbon disulfide 
• 74-85-1 ethene 
• 57-57-8 β-Propiolactone 
• 71-43-2 benzene 
• 64-17-5 ethanol 
• 936-59-4 3-chloropropiophenone 
• 127-08-2 potassium acetate 
• 14088-57-4 2-diazo-1-phenyl-1-propanone 
• 7334-41-0 3-acetoxypropiophenone 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 37559-18-5 3-phenylprop-2-ynyl acetate 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 51011-65-5 2,3-dibromo-1-phenylpropan-1-one 
• 94-38-2 3-diethylamino-1-phenyl-propan-1-one 

Downstream Products

• 60868-01-1 3-(4-methylpiperazin-1-yl)-1-phenylpropan-1-one 
• 97785-35-8 1,3-dimethyl-7-(3-oxo-3-phenyl-propyl)-3,7-dihydro-purine-2,6-dione 
• 6056-35-5 endo-2-benzoyl-5-norbornene 
• 464-66-4 nepenthone 
• 101891-03-6 phenyl-(6-phenyl-3,4-dihydro-2H-pyran-2-yl)-ketone thiosemicarbazone 
• 3506-36-3 3-dimethylaminopropiophenone 
• 831-14-1 cyclohex-3-en-1-yl(phenyl)methanone 
• 2983-48-4 1-phenyl-3-(phenylamino)propan-1-one 
• 6337-36-6 2-Benzoyl-6-phenyl-3,4-dihydro-2H-pyran 
• 56544-22-0 3-ethoxy-1-phenyl-propan-1-one-(2,4-dinitro-phenylhydrazone) 
• 17109-21-6 1-phenyl-propenone-((E)-2,4-dinitro-phenylhydrazone) 
• 58337-98-7 1,2,5-triphenylpentane-1,5-dione 
• 99069-98-4 1-methoxymethyl-2-oxo-2-phenyl-ethylmercury ⁽¹⁺⁾; bromide 
• 4055-00-9 6-phenyl-3,4-dihydropyran-2-one 

Relevant academic research and scientific papers

Copper-catalyzed three-component: N -alkylation of quinazolinones and azoles

A Cu-catalyzed three-component N-alkylation coupling reaction of N-heteroarenes with methyl ketones and DMPA as a carbon source has been developed. Using methyl ketones as alkylation reagents and DMPA (N,N′-dimethylpropionamide) as a carbon source, the re

Copper-catalyzed multiple oxidation and cycloaddition of aryl-alkyl ketones (alcohols) for the synthesis of 4-acyl- and 4-diketo-1,2,3-triazoles

A Cu/TEMPO-catalyzed tandem multiple oxidative dehydrogenation and cycloaddition has been developed, which affords 4-acyl-1,2,3-triazoles and 4-diketo-1,2,3-triazoles from readily-available aryl-alkyl ketones (or alcohols) and different organic azides. Moreover, the reaction used environmentally friendly dimethyl carbonate (DMC) as the solvent and air as the oxidant, and H2O was the only by-product, so it provides a green and practical synthetic method for 1,2,3-triazoles.

Electrochemically driven desaturation of carbonyl compounds

Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access such structures from enol silanes and phosphates using electrons as the primary reagent. This electrochemically driven desaturation exhibits a broad scope across an array of carbonyl derivatives, is easily scalable (1–100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway. [Figure not available: see fulltext.]

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Synthesis of β-hydroxyenones and its application toward development of tetrahydro-4H-pyran-4-one in an atom-economic fashion is limited. This manuscript describes a ruthenium-catalyzed atom-economic coupling of pent-2-yne-1,5-diols and Michael acceptors as an efficient route for the synthesis of β-hydroxyenones with excellent yields and high regioselectivity. The β-hydroxyenones further undergo a 6-endo trig cyclization under acid-catalyzed conditions to deliver the tetrahydro-4H-pyran-4-ones with high diastereoselectivity. An intramolecular aldol condensation under mild basic conditions and palladium-catalyzed oxidative aromatization was developed for the synthesis of hexahydro-6H-isochromen-6-ones and isochromanols, respectively, from highly substituted tetrahydro-4H-pyran-4-ones with excellent yield and diastereoselectivity. Overall, this work demonstrates the synthetic potential toward the synthesis of oxacycles like tetrahydro-4H-pyran-4-ones, hexahydro-6H-isochromen-6-ones, and isochromanols via an atom-economic catalysis.

Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol

Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).