5440-80-2

Usage

Uses

Used in the Food Industry:
1-(4-methoxyphenyl)pentan-3-one is used as a flavoring agent for adding a sweet and floral aroma to a wide range of products, enhancing the sensory experience for consumers.
Used in the Perfume and Fragrance Industry:
PMPK is utilized as a key component in the production of perfumes and fragrances, capitalizing on its pleasant scent to create desirable and long-lasting scents.
Used in Pharmaceutical Applications:
1-(4-methoxyphenyl)pentan-3-one is being explored for its potential therapeutic properties, indicating a promising future in the pharmaceutical sector. Its study and development are ongoing to unlock its full potential in healthcare.

Upstream product

• 104-27-8 1-(4-methoxy-phenyl)-pent-1-en-3-one 
• 208453-06-9 3-(4-methoxyphenyl)propionic acid ethanethiol ester 
• 999-75-7 ethylzinc iodide 
• 82297-64-1 (E)-1-(4-methoxyphenyl)pent-1-en-3-one 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 616-25-1 1-Penten-3-ol 
• 683226-13-3 3-(4-methoxyphenyl)-thiopropionic acid (S)-dodecyl ester 
• 557-20-0 diethylzinc 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 925-90-6 ethylmagnesium bromide 
• 749927-93-3 N-methoxy-N-methyl-3-(4-methoxyphenyl)propionamide 
• 623-12-1 4-chloromethoxybenzene 
• 1629-58-9 4-penten-3-one 

Downstream Products

• 219717-33-6 5-(p-methoxyphenyl)-3-methylpentan-3-ol 

Relevant academic research and scientific papers

Palladium-catalyzed room temperature acylative cross-coupling of activated amides with trialkylboranes

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts

Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions were catalyzed by phosphorus-free palladium precursors modified with the menthol-substituted imidazolium chlorides. Formation of crystalline palladium nanoparticles, of the diameter up to 65 nm, in the reaction mixture was evidenced by TEM.

Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation

Chitin-supported palladium and iridium catalysts (i.e., Pd/chitin, Ir/chitin) successfully promote the hydrogen borrowing C–C bond formation reaction to afford phytochemicals and aroma compounds in excellent yields.

Multifunctional supported bimetallic catalysts for a cascade reaction with hydrogen auto transfer: Synthesis of 4-phenylbutan-2-ones from 4-methoxybenzyl alcohols

We report the one-pot tandem synthesis of 4-(4-methoxyphenyl)butan-2-one directly from 4-methoxybenzyl alcohol and acetone using a multifunctional supported AuPd nanoalloy catalyst. This one-pot synthesis involves dehydrogenation, aldol condensation and hydrogenation of CC. In this supported AuPd catalyst, the bimetallic sites catalyse the dehydrogenation and hydrogenation steps and, in combination with the support, catalyse the C-C coupling (aldol) process. This supported bimetallic catalyst is also effective in utilizing hydrogen from the dehydrogenation reaction for the hydrogenation of 4-(4-methoxyphenyl)but-3-en-2-one to 4-(4-methoxyphenyl)butane-2-one via a hydrogen auto transfer route. These multifunctional catalysts were characterised using transmission electron microscopy, X-ray diffraction and X-ray photoelectron spectroscopy.

Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids

A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.

2-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated ketones under ligand-free and neutral conditions

A simple and efficient Ru-catalyzed conjugate addition reaction of arylboronic acids to α,β-unsaturated ketones under neutral conditions without any additional ligands has been developed. This Ru(II)-catalytic system both fulfilled the inhibition of the β-hydride elimination in the catalytic cycle and minimized the protonolysis of arylboronic acids.

Synthesis of acylsilanes by palladium-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides

An acylsilane synthesis by a Pd-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides was developed. S-Phenyl thiol esters with a variety of functional groups were converted to corresponding acylsilanes.

Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates

Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were prepared in good to excellent yields from the corresponding unsaturated carbonyl compounds. They were shown to be effective coupling partners in the Suzuki-Miyaura reaction with a variety of electrophiles including electron-rich and electron-poor aryl bromides and -chlorides.

A practical synthesis of multifunctional ketones through the fukuyama coupling reaction

A highly efficient, robust and scalable protocol for the synthesis of multifunctional ketones through Fukuyama coupling, i.e., cross-coupling of thiol esters with zinc reagents, has been developed. Treatment of thiol esters with alkylzinc iodides or dialkyl zincs in the presence of palladium on activated carbon (Pd/C) or palladium acetate [Pd(OAc)2] furnished the corresponding ketones in high yields. Evaluation of the properties-activities relationship of the Pd/C-catalyzed reaction has proven that oxidic Pd/C is much more potent than reduced Pd/C in the reaction of thiolactone la with zinc reagent 2a. Based on the dependence of the Pd/C-catalyzed reaction on the nature of Pd/C in combination with the extent of the Pd leaching from Pd/C to the solution, a dual reaction mechanism for the Pd/C-catalyzed Fukuyama coupling reaction, which includes heterogeneous and homogeneous catalytic cycles, was proposed. The marked reduction of the zinc reagents and the use of Pd(OAc) 2 in much smaller amounts were achieved when zinc bromide was added. This supports a hypothesis where a shift of the Schlenk equilibrium from inactive dialkylzincs (R2Zn) to active organozinc species, such as alkylzinc halides (RZnX) and three-coordinate species [(RZnX2) -. (ZnX)+], and generation of the stabilized monomeric Pd complexes during the reaction, may facilitate the reaction.

Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same

The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1 and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.