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

• 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 
• 51011-65-5 2,3-dibromo-1-phenylpropan-1-one 
• 170695-97-3 vinyl phenyl ketone dimethyl acetal 
• 5409-66-5 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 
• 70013-89-7 1-benzoylethylpyridinium chloride 
• 60-29-7 diethyl ether 

Downstream Products

• 60868-01-1 3-(4-methylpiperazin-1-yl)-1-phenylpropan-1-one 
• 111510-92-0 3-(5-methylfuran-2-yl)-1-phenylpropan-1-one 
• 6056-35-5 endo-2-benzoyl-5-norbornene 
• 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 
• 2538-52-5 1,3-diphenyl-4,5-dihydro-1H-pyrazole 
• 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 
• 855288-74-3 phenyl[1, 1’; 4’, 1’’]terphenyl-2’-yl-methanone 
• 92963-42-3 4-nitro-1,4-diphenyl-butan-1-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.

Cobalt(II)-Catalyzed C?H/N?H Functionalization and Annulation of N-(quinolin-8-yl)benzamide with Cyclopropanols

A new method for Co-catalyzed C?H/N?H functionalization and [4+1] annulation of N-(quinolin-8-yl)benzamide with cyclopropanols was developed. This protocol tolerates a variety of functional groups, thereby providing an efficient method for the fabrication of isoindolin-1-ones. Moreover, the utility of this strategy was showcased by the late-stage modification of lithocholic acid derivatives and ibuprofen derivatives.

Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,?-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.

Enantioselective Copper-Catalyzed Electrophilic Sulfenylation of Cyclic Imino Esters

Herein we report an enantioselective sulfenylation of cyclic imino esters with the efficient and versatile sulfenylation reagent S-alkyl 4-methylbenzenesulfonothioates. By utilizing the Cu/tBu-Phosferrox catalytic system, we can assemble diverse S-alkyl groups into the cyclic imino esters under mild conditions in good yields and with excellent enantioselectivities. Remarkably, this method demonstrates a high tolerance of diverse functional groups and proves to be applicable in the late-stage functionalization of pharmaceuticals.

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.

Diastereoselective Photoredox-Catalyzed [3 + 2] Cycloadditions of N-Sulfonyl Cyclopropylamines with Electron-Deficient Olefins

A highly diastereoselective, visible-light-induced [3 + 2] cycloaddition between N-sulfonyl cyclopropylamines and electron-deficient olefins is reported. The reactions proceed via the oxidation of a sulfonamide aza-anion by an organic photocatalyst to generate a nitrogen-centered radical. Strain-induced ring opening and intermolecular addition to the olefin generate an intermediate carbon-centered radical that is reduced to an anion prior to 5-exo cyclization. This enables a highly diastereoselective construction of trans-cyclopentanes possessing synthetically useful functional groups.

Isotope Effects and the Mechanism of Photoredox-Promoted [2 + 2] Cycloadditions of Enones

13C kinetic isotope effects (KIEs) for the photoredox-promoted [2 + 2] cycloaddition of enones were determined in homocoupling and heterocoupling examples. The only significant KIEs were observed at the β carbon, indicating that Cβ-Cβ bond formation is irreversible. However, these KIEs were much lower than computational predictions, suggesting that product selectivity is determined in part by a step prior to Cβ-Cβ bond formation. The results are explained as arising from a competition between C-C bond formation and electron exchange between substrate alkenes. This idea is supported by a relatively small substituent effect on substrate selectivity. The possible rates for electron transfer and bond-forming steps are analyzed, and the competition appears plausible, particularly if the mechanism involves a complex between reduced and neutral enone molecules.

Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease

The protozoan parasite Trypanosoma cruzi is the causative agent of Chagas disease, the most important parasitic infection in Latin America. The only treatments currently available are nitro-derivative drugs that are characterised by high toxicity and limited efficacy. Therefore, there is an urgent need for more effective, less toxic therapeutic agents. We have previously identified the potential for Mannich base derivatives as novel inhibitors of this parasite. To further explore this family of compounds, we synthesised a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage. We ultimately identified derivative 3c, which demonstrated excellent trypanocidal properties, and a synergistic mode of action against trypomastigotes in combination with the reference drug benznidazole. Both its druggability and low-cost production make this derivative a promising candidate for the preclinical, in vivo assays of the Chagas disease drug-discovery pipeline.