36939-02-3

Usage

Ketone derivative

It is a derivative of a ketone, which is a compound with a carbonyl group (C=O) bonded to two carbon atoms.

Phenyl group attachment

First carbon of the propyl chain
A phenyl group (a ring of six carbon atoms with delocalized electrons) is attached to the first carbon atom of the propyl chain (three-carbon chain).

Pyridin-4-yl group attachment

Third carbon of the propyl chain
A pyridin-4-yl group (a six-membered nitrogen-containing ring with five carbon atoms and one nitrogen atom) is attached to the third carbon atom of the propyl chain.

Chemical reactivity

The compound can participate in various chemical reactions and synthesis processes due to the presence of its functional groups (carbonyl and aromatic rings).

Potential pharmacological uses

The compound may have potential applications in the field of medicine, but further research and studies are needed to determine its specific properties and applications.

Upstream product

• 925702-34-7 N-methoxy-N-methyl-3-pyridin-4-ylpropionamide 
• 100-58-3 phenylmagnesium bromide 
• 586-95-8 pyridine-4-methanol 
• 98-86-2 acetophenone 
• 2057-49-0 4-(3-phenylpropyl)pyridine 
• 100-43-6 4-vinylpyridine 
• 100-52-7 benzaldehyde 
• 98-85-1 1-Phenylethanol 
• 1074-12-0 phenylglyoxal hydrate 
• 5908-41-8 benzoyltrimethylsilane 

Downstream Products

• 925702-36-9 2-phenyl-3-(pyridin-4-ylmethyl)quinoline-4-carboxylic acid trifluoroacetate 

Relevant academic research and scientific papers

Palladium-Catalyzed Siloxycyclopropanation of Alkenes Using Acylsilanes

Currently, catalytically transferable carbenes are limited to electron-deficient and neutral derivatives, and electron-rich carbenes bearing an alkoxy group (i.e., Fischer-type carbenes) cannot be used in catalytic cyclopropanation because of the lack of appropriate carbene precursors. We report herein that acylsilanes can serve as a source of electron-rich carbenes under palladium catalysis, enabling cyclopropanation of a range of alkenes. This reactivity profile is in sharp contrast to that of metal-free siloxycarbenes, which are unreactive toward normal alkenes. The resulting siloxycyclopropanes serve as valuable homoenolate equivalents, allowing rapid access to elaborate β-functionalized ketones.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Phosphine-free pincer-ruthenium catalyzed biofuel production: High rates, yields and turnovers of solventless alcohol alkylation

Phosphine-free pincer-ruthenium carbonyl complexes based on bis(imino)pyridine and 2,6-bis(benzimidazole-2-yl) pyridine ligands have been synthesized. For the β-alkylation of 1-phenyl ethanol with benzyl alcohol at 140 °C under solvent-free conditions, (Cy2NNN)RuCl2(CO) (0.00025 mol%) in combination with NaOH (2.5 mol%) was highly efficient (ca. 93% yield, 372?000 TON at 12?000 TO h-1). These are the highest reported values hitherto for a ruthenium based catalyst. The β-alkylation of various alcohol combinations was accomplished with ease which culminated to give 380?000 TON at 19?000 TO h-1 for the β-alkylation of 1-phenyl ethanol with 3-methoxy benzyl alcohol. DFT studies were complementary to mechanistic studies and indicate the β-hydride elimination step involving the extrusion of acetophenone to be the overall RDS. While the hydrogenation step is favored for the formation of α-alkylated ketone, the alcoholysis step is preferred for the formation of β-alkylated alcohol. The studies were extended for the upgradation of ethanol to biofuels. Among the pincer-ruthenium complexes based on bis(imino)pyridine, (Cy2NNN)RuCl2(CO) provided high productivity (335 TON at 170 TO h-1). Sterically more open pincer-ruthenium complexes such as (Bim2NNN)RuCl2(CO) based on the 2,6-bis(benzimidazole-2-yl) pyridine ligand demonstrated better reactivity and gave not only good ethanol conversion (ca. 58%) but also high turnovers (ca. 2100) with a good rate (ca. 710 TO h-1). Kinetic studies indicate first order dependence on concentration of both the catalyst and ethanol. Phosphine-free catalytic systems operating with unprecedented activity at a very low base loading to couple lower alcohols to higher alcohols of fuel and pharmaceutical importance are the salient features of this report. This journal is

Selective C(sp3)?H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

A mild and selective C(sp3)?H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C?H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (?)-ambroxide, pregnenolone acetate, (+)-sclareolide, and artemisinin, exemplifies the utility of this new method.

Combined Iron/Hydroxytriazole Dual Catalytic System for Site Selective Oxidation Adjacent to Azaheterocycles

This report details a new method for site-selective methylene oxidation adjacent to azaheterocycles. A dual catalysis approach, utilizing both an iron Lewis acid and an organic hydroxylamine catalyst, proved highly effective. We demonstrate that this method provides complementary selectivity to other known catalytic approaches and represents an improvement over current heterocycle-selective reactions that rely on stoichiometric activation.

Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols

An ionic cobalt-PNP complex is developed for the efficient α-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.

Vinylpyridines as Building Blocks for the Photocatalyzed Synthesis of Alkylpyridines

The photocatalyzed addition of several hydrogen donors (ethers, aldehydes, alkanes, amides) onto vinylpyridines was achieved. This approach provided access to alkylpyridines, which are important building blocks for the preparation of compounds with biological activity. The strategy was very simple and straightforward because it required only a small amount of a cheap decatungstate salt as photocatalyst. As an added advantage, the reaction could be performed under sunlight irradiation as well as under flow conditions.

Rhodium-catalyzed alkylation of ketones and alcohols with alcohols

An efficient method for direct alkylation of ketones and alcohols through the borrowing hydrogen strategy in the presence of rhodium complexes as catalyst was developed. This transformation is tolerant to various functional substrates and is efficient in C-C coupling of primary and secondary alcohols, which provides an alternative method of the synthesis of functional ketones from simple and commercially available materials.

Comparative Study of the Limitations and Challenges in Atom-Transfer C-H Oxidations

A comparative study is disclosed that seeks to highlight the current limitations and challenges that exist in the field of atom-transfer C-H oxidations. State-of-the-art methods are benchmarked in order to showcase clear differences and similarities. A novel Mn-mediated method for C-H oxidation is disclosed that serves as a rapid and simple method for aliphatic C-H hydroxylation. Finally, two methods that allow for C-H oxidation in the presence of pyridine-containing substrates are studied, something that is rare in the field but of great interest to the chemical community.