2430-99-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-METHYLPHENYL)ACETOPHENONE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(4-METHYLPHENYL)ACETOPHENONE is utilized as a building block in the production of agrochemicals, aiding in the creation of compounds that can enhance crop protection and yield.
Used in Organic Synthesis:
2-(4-METHYLPHENYL)ACETOPHENONE is employed as a versatile intermediate in organic synthesis for its reactivity and capacity to form a wide range of organic compounds, contributing to the advancement of chemical research and product development.

InChI:InChI=1/C15H14O/c1-12-7-9-13(10-8-12)11-15(16)14-5-3-2-4-6-14/h2-10H,11H2,1H3

Upstream product

• 22440-35-3 2-phenyl-3-p-tolyl-oxirane 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 532-27-4 1-chloroacetophenone 
• 108-88-3 toluene 
• 80351-85-5 N-Benzyl-N-[(4-methyl-benzylsulfanyl)-phenyl-methyl]-benzamide 
• 26067-92-5 2-amino-1-phenyl-1-p-tolyl-ethanol 
• 64-19-7 acetic acid 
• 34921-09-0 diethyl (4-methylbenzyl) phosphate 
• 98-88-4 benzoyl chloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 104-85-8 para-methylbenzonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 201230-82-2 carbon monoxide 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 65-85-0 benzoic acid 
• 2431-02-9 2-hydroxy-1-phenyl-2-p-tolyl-ethanone 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 30203-87-3 1-chloro-4-(4-methylbenzyl)benzene 
• 22865-60-7 1-(4-methoxybenzyl)-4-methylbenzene 
• 30203-93-1 4-[(4-methylphenyl)methyl]-1,1’-biphenyl 
• 1222465-77-1 4-methyl-1-phenyl-2-p-tolylpent-4-en-1-one 
• 1384131-13-8 (Z)-1-t-butyldimethylsilyloxy-2-(4-methylphenyl)-1-phenylethene 
• 56074-58-9 α,α-bis(4-methylphenyl)acetophenone 
• 1443223-36-6 1-phenyl-2-m-tolyl-2-p-tolylethanone 
• 1448819-76-8 5-methyl-1-phenethyl-2-phenyl-3-p-tolyl-1H-pyrrole 
• 1448819-69-9 1-hexyl-2-phenyl-3-p-tolyl-1H-pyrrole 
• 1448819-79-1 1-hexyl-5-methyl-2-phenyl-3-p-tolyl-1H-pyrrole 
• 1448819-83-7 2-phenyl-3-(4-methylphenyl)pyrrole 

Relevant academic research and scientific papers

H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water

An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2H-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.

Oxaprozin Analogues as Selective RXR Agonists with Superior Properties and Pharmacokinetics

The retinoid X receptors (RXR) are ligand-activated transcription factors involved in multiple regulatory networks as universal heterodimer partners for nuclear receptors. Despite their high therapeutic potential in many pathologies, targeting of RXR has only been exploited in cancer treatment as the currently available RXR agonists suffer from exceptional lipophilicity, poor pharmacokinetics (PK), and adverse effects. Aiming to overcome the limitations and to provide improved RXR ligands, we developed a new potent RXR ligand chemotype based on the nonsteroidal anti-inflammatory drug oxaprozin. Systematic structure-activity relationship analysis enabled structural optimization toward low nanomolar potency similar to the well-established rexinoids. Cocrystal structures of the most active derivatives demonstrated orthosteric binding, and in vivo profiling revealed superior PK properties compared to current RXR agonists. The optimized compounds were highly selective for RXR activation and induced RXR-regulated gene expression in native cellular and in vivo settings suggesting them as excellent chemical tools to further explore the therapeutic potential of RXR.

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation

The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].