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Usage

Uses

Used in Pharmaceutical Industry:
4'-Methylvalerophenone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to serve as a building block for the development of new drugs with potentially improved properties, such as enhanced efficacy, selectivity, or reduced side effects.
Used in Chemical Research:
4'-Methylvalerophenone is used as a research tool in the study of photochemical processes and the behavior of aromatic ketones under different conditions. Its unique structure can provide valuable insights into the reactivity and stability of similar compounds, contributing to the advancement of chemical knowledge and the development of new synthetic strategies.
Used in Enzyme Inhibition Studies:
As a derivative of Valerophenone, which is known to be an inhibitor of the enzyme carbonyl reductase, 4'-Methylvalerophenone may also be used in enzyme inhibition studies. Its potential to modulate enzyme activity can be explored for the development of new therapeutic agents targeting specific metabolic pathways or diseases.

Upstream product

• 638-29-9 n-valeryl chloride 
• 108-88-3 toluene 
• 1889-20-9 n-butylmagnesium iodide 
• 104-85-8 para-methylbenzonitrile 
• 109-52-4 valeric acid 
• 3115-66-0 tetra-n-butylphosphonium iodide 
• 109-65-9 1-bromo-butane 
• 64874-44-8 p-tolyl(phenylthio)sulfine 
• 7664-39-3 hydrogen fluoride 
• 110-59-8 pentanonitrile 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 109-72-8 n-butyllithium 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 10415-86-8 p-tolyl valerate 
• 122-00-9 para-methylacetophenone 
• 850352-48-6 2-bromo-1-(4-methylphenyl)pentan-1-one 
• 81392-97-4 (E)-1-methyl-4-(pent-1-en-1-yl)benzene 
• 360-34-9 1,1,1-trifluoro-2-hexanone 
• 94-08-6 4-methylbenzoic acid ethyl ester 

Relevant academic research and scientific papers

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Efficient Organoruthenium Catalysts for α-Alkylation of Ketones and Amide with Alcohols: Synthesis of Quinolines via Hydrogen Borrowing Strategy and their Mechanistic Studies

A new family of phosphine free organometallic ruthenium(II) catalysts (Ru1–Ru4) supported by bidentate NN Schiff base ligands (L1–L4 where L1=N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazineylidene)methyl) aniline, L2=N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazineylidene)methyl)aniline, L3=N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazineylidene)methyl)- aniline and L4=N,N-diethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazineylidene)methyl) aniline) was prepared and characterized. These half-sandwich complexes acted as catalysts for C?C bond formation and exhibited excellent performance in the dehydrogenative coupling of ketones and amides. In the synthesis of C–C bonds, alcohols were utilized as the alkylating agent. A broad range of substrates, including sterically hindered ketones and alcohols, were well tolerated under the optimized conditions (TON up to 47000 and TOF up to 11750 h?1). This ruthenium (II) catalysts were also active towards the dehydrogenative cyclization of o-amino benzyl alcohol for the formation of quinolines derivatives. Various polysubstituted quinolines were synthesized in moderate to excellent yields (TON up to 71000 and TOF up to 11830 h?1). Control experiments were carried out and the ruthenium hydride intermediate was characterized to support the reaction mechanism and a probable reaction pathway of dehydrogenative coupling for the C?C bond formation has been proposed.

Suzuki-Miyaura coupling of simple ketones via activation of unstrained carbon-carbon bonds

Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic ketones. Preliminary mechanistic study suggests that the ketone α-C-C bond was cleaved via oxidative addition.

Co (II)-C12 alkyl carbon chain multi-functional ionic liquid immobilized on nano-SiO2 nano-SiO2@CoCl3-C12IL as an efficient cooperative catalyst for C–H activation by direct acylation of aryl halides with aldehydes

Nano-silica supported ionic liquids composed of alkyl carbon chain and transition metal chlorides anions have been prepared and successfully applied as a heterogeneous catalyst in the direct aldehyde C-H activation. Catalytic results indicated that nano-SiO2 supported ionic liquid consisting C12 alkyl carbon chain and CoCl3 anion nano-SiO2@CoCl3-C12IL showed excellent catalytic properties with good to excellent yields towards the desired aryl ketones. The excellent recyclability of the supported catalyst, mild reaction conditions, low catalyst loading, and operational simplicity are the important features of this methodology.

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

One-pot sequential 1,2-addition, Pd-catalysed cross-coupling of organolithium reagents with Weinreb amides

An efficient sequential 1,2-addition/cross-coupling of Weinreb amides with two organolithium reagents is reported. This synthetic approach allows access to a wide variety of functionalized ketones in a modular way. The one-pot procedure presented here takes advantage of a kinetically stable tetrahedral Weinreb intermediate during subsequent Pd-catalyzed cross-coupling with the second organolithium reagent leading, within short reaction times and under mild conditions, to the formation of ketones in excellent overall yields.

Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: Application to efficient one-pot synthesis of ketones and aldehydes from esters

Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83-95% yields and aldehydes quantitatively.

An effective one-pot conversion of acid chlorides to aldehydes and ketones

Aldehydes and ketones were synthesized from their respective acid chlorides via a one-pot protocol. Morpholine amide intermediates that were readily prepared by the aminolysis of various acid chlorides with diisobutyl(morpholino) aluminum smoothly reacted with the reducing agent LDBMA and the organolithium reagents under mild reaction conditions (0 C), giving almost excellent product yields of up to 95%.

A Palladium Bipyridyl Complex Grafted onto Nanosized MCM-41 as a Heterogeneous Catalyst for Negishi Coupling

The Negishi coupling of aryl bromides or acyl chlorides with organozinc chlorides catalyzed by a palladium bipyridyl complex anchored on nanosized mobile crystalline material 41 (MCM-41) were investigated. The reactions proceeded smoothly with a very low catalyst loading in THF at 70°C for electron-deficient aryl bromides, which gave good to high yields of the Negishi coupling products. However, reactions in toluene at 110°C were required if electron-rich aryl bromides were employed. For acyl chlorides, the reactions could be performed in THF at 50°C and the corresponding ketones and ynones were obtained in high yields. After centrifugation, it was possible to easily recover the supported catalyst from the reaction mixture, and this could be reused several times without any retreatment or regeneration with only a slight decrease in activity.

Direct synthesis of aryl ketones by palladium-catalyzed desulfinative addition of sodium sulfinates to nitriles

Mild yet direct: A convenient and efficient method for the synthesis of various aryl ketones by palladium-catalyzed desulfinative addition of aromatic sulfinic acid sodium salts to various nitriles is described (see scheme). Aromatic and aliphatic nitriles are successfully reacted with arenesulfinic acid sodium salts to form aryl ketones in good yields.