3160-32-5

Usage

Uses

Used in Chemical Synthesis:
4-methyl-1-phenylpent-1-en-3-one is utilized as an intermediate in the synthesis of a variety of other organic compounds. Its unique structure allows it to be a key component in creating complex molecules.
Used in Fine Chemicals Production:
4-methyl-1-phenylpent-1-en-3-one serves as a common building block in the production of fine chemicals, where its specific reactivity and structural features are leveraged to create high-quality specialty products.
Used in Pharmaceutical Industry:
4-methyl-1-phenylpent-1-en-3-one is used as a precursor in the development of pharmaceuticals, contributing to the creation of new drugs and improving existing ones through its chemical properties.
Used in Agrochemicals Production:
In the agrochemical sector, 4-methyl-1-phenylpent-1-en-3-one is employed in the synthesis of various agrochemicals, playing a crucial role in the development of effective products for agricultural applications.
Overall, 4-methyl-1-phenylpent-1-en-3-one's diverse applications across different industries highlight its importance and versatility as a chemical intermediate and building block.

InChI:InChI=1/C12H14O/c1-10(2)12(13)9-8-11-6-4-3-5-7-11/h3-10H,1-2H3/b9-8+

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 100-52-7 benzaldehyde 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 1068-55-9 isopropylmagnesium chloride 
• 1902-93-8 3-Ethoxy-4-methyl-1-phenyl-pent-1-in 
• 130739-62-7 Methyl(4-methyl-3-oxo-1-phenylpentyl)propanedioic acid, diethyl ester 
• 86983-95-1 (1E)-4-methyl-1-phenylpent-1-en-3-ol 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 19967-55-6 1-bromo-3-methyl-2-butanone 
• 84104-02-9 2-(isopropyl)-2-morpholino-4-phenyl-3-butenenitrile 
• 22915-20-4 4-phenyl-2-piperidin-1-yl-but-3-enenitrile 
• 75-26-3 isopropyl bromide 
• 4440-01-1 lithium phenylacetylide 
• 64-18-6 formic acid 

Downstream Products

• 859950-94-0 2-bromo-4-methyl-1,1-diphenyl-pentan-3-one 
• 46969-58-8 4-methyl-1-morpholin-4-yl-1-phenyl-pentan-3-one 
• 58371-19-0 (Z)-3-Hydroxy-3-isopropyl-2-methylene-5-phenyl-pent-4-enoic acid methyl ester 
• 125564-00-3 (E)-5-[(2-Dimethylamino-ethyl)-methyl-amino]-4,4-dimethyl-1-phenyl-pent-1-en-3-one; hydrobromide 
• 125563-99-7 (E)-5-[(2-Diethylamino-ethyl)-methyl-amino]-4,4-dimethyl-1-phenyl-pent-1-en-3-one; hydrobromide 
• 125563-89-5 (E)-5-Diethylamino-4,4-dimethyl-1-phenyl-pent-1-en-3-one; hydrobromide 
• 40463-09-0 4-methyl-1-phenylpentan-3-one 
• 53243-88-2 benzylidene isopropyl ketoxime 
• 132843-52-8 3,3-dimethyl-4-oxo-6-phenyl-3,4-dihydro-1,2-dithiine 
• 132843-51-7 bis (4-methyl-1-phenyl-3-oxopentyl)disulfure 
• 110519-66-9 3-Isobutyryl-2,2-dimethyl-4,5-diphenyl-cyclohexanone 
• 125564-04-7 (E)-4-Bromo-4-methyl-1-phenyl-pent-1-en-3-one 
• 5435-09-6 (4-methyl-3-oxo-1-phenyl-pentyl)-malonic acid diethyl ester 
• 1027251-58-6 8-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-phenyl-oct-6-yn-3-one 

Relevant academic research and scientific papers

Antimicrobial evaluation of some styryl ketone derivatives and related thiol adducts

Acyclic α,β-unsaturated ketones were synthesized and treated with either 2-mercaptoethanol or cystenamine hydrochloride under the simulated physiological conditions. The thiol group of these model biological nucleophiles underwent Michael type addition to the activated double bond. The incubation of the bis-Mannich base of 3-benzylidene-2,4-pentanedione with 2-mercaptoethanol, surprisingly, gave rise to the formation of 5-[(2- hydroxyethyl)thio]-1-phenyl-1-penten-3-one (8) in low yield. Evaluation of the compounds versus Gram-positive and Gram-negative bacteria and also a type of fungus indicated that the conjugated ketones and their adducts, except the bis-Mannich base, have antimicrobial activity at 10 μg/mL. The Mannich base, 3, showed antibacterial property against only Escherichia coli at 1000 μg/mL in spite of containing a bioactive styryl ketone structure and having deamination ability. However, the thiol adducts, which do not contain any α,β-unsaturated ketone function, exhibited similar antimicrobial potency to the conjugated ketone derivatives, possibly due to the exchange reaction with enzymes or coenzymes in the microorganisms.

Formal [4+2] cycloaddition of 3-phenylcyclobutanones with nitriles

Various 3-phenylcyclobutanones reacted with aliphatic and aromatic nitriles in the presence of Me3SiOTf to afford dihydropyridones by formal [4+2] cycloaddition.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex

Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes

We report the enantioselective formation of quaternary stereogenic centers by the intermolecular addition of malononitrile, an acyl anion equivalent, and related pronucleophiles to several 1,3-disubstituted acyclic 1,3-dienes in the presence of a Pd-PHOX catalyst. Products are obtained in up to 88% yield and 99:1 er and in most cases are formed as a single regioisomer. The products' malononitrile unit undergoes oxidative functionalization to afford β,γ-unsaturated carbonyls bearing internal olefins and α-quaternary stereogenic centers.

Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones

Asymmetric synthesis of 2-cyclopentenones was achieved by chirality transfer based on Lewis acid catalyzed decarboxylative Nazarov cyclization of optically active cyclic enol carbonates, which are prepared by silver-catalyzed carbon dioxide incorporation into optically pure propargyl alcohols. The stereochemistry at the 4,5-positions of the 2-cyclopentenones was cleanly constructed by reflecting the stereochemistry of the starting materials. This method could be applied to various substrates to obtain the corresponding products in high yields with highly efficient chirality transfer.

Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes

A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.

Formal [4?+?4] cycloaddition of 3-arylcyclobutanones with anthracene and their acid-promoted intramolecular cyclization with skeletal rearrangement

A reaction of 3-arylcyclobutanones with anthracene in the presence of TiCl4 gave 14-aryl-9,10-dihydro-9,10-butanoanthracen-12-ones as a formal [4 + 4] cycloadduct of anthracenes with a C4 unit formed by cleaving the more substituted C2–C3 bond of cyclobutanones. On the other hand, activation of 3-arylcyclobutanones with TfOH in the absence of nucleophiles gave 2-tetralones with skeletal rearrangement.

Friedel-Crafts Alkylation of Aromatics by TiCl 4 -Promoted Ring Cleavage of 3-Arylcyclobutanones

Ring cleavage of 3-arylcyclobutanones and successive Friedel-Crafts alkylation of methoxy- or alkyl-substituted benzene derivatives proceeded to give 3,3-diarylbutan-2-ones by activation with titanium tetrachloride.