25233-52-7

Usage

Uses

Used in Pharmaceutical Industry:
N-(3,5-dimethylphenyl)-3-oxobutanamide is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure and properties make it a valuable component in the development of new medications with potential therapeutic applications in treating a range of illnesses and diseases.
Used in Drug Development:
N-(3,5-dimethylphenyl)-3-oxobutanamide is used in drug development for its potential therapeutic applications. Its pharmacological properties allow it to be a key component in the creation of new medications that can address various health conditions and improve patient outcomes.

InChI:InChI=1/C12H15NO2/c1-8-4-9(2)6-11(5-8)13-12(15)7-10(3)14/h4-6H,7H2,1-3H3,(H,13,15)

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 108-69-0 3,5-dimethylaminoaniline 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1694-31-1 tert-butyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 1353748-63-6 C₁₉H₁₉N₃O₃ 
• 1353748-56-7 C₁₇H₂₀N₂O₅ 
• 108463-45-2 1,4,5,7-Tetramethyl-2(1H)-quinolinone 
• 31009-97-9 2-Chloracetessigsaeure-3,5-dimethylanilid 

Relevant academic research and scientific papers

Heteroaryl Phosphonates as Noncovalent Inhibitors of Both Serine- and Metallocarbapenemases

Gram-negative pathogens expressing serine β-lactamases (SBLs) and metallo-β-lactamases (MBLs), especially those with carbapenemase activity, threaten the clinical utility of almost all β-lactam antibiotics. Here we describe the discovery of a heteroaryl phosphonate scaffold that exhibits noncovalent cross-class inhibition of representative carbapenemases, specifically the SBL KPC-2 and the MBLs NDM-1 and VIM-2. The most potent lead, compound 16, exhibited low nM to low μM inhibition of KPC-2, NDM-1, and VIM-2. Compound 16 potentiated imipenem efficacy against resistant clinical and laboratory bacterial strains expressing carbapenemases while showing some cytotoxicity toward human HEK293T cells only at concentrations above 100 μg/mL. Complex structures with KPC-2, NDM-1, and VIM-2 demonstrate how these inhibitors achieve high binding affinity to both enzyme classes. These findings provide a structurally and mechanistically new scaffold for drug discovery targeting multidrug resistant Gram-negative pathogens and more generally highlight the active site features of carbapenemases that can be leveraged for lead discovery.

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Multicomponent strategy to indeno[2,1- C ]pyridine and hydroisoquinoline derivatives through cleavage of carbon-carbon bond

A concise and efficient three-component domino reaction has been developed for the synthesis of polyfunctionalized indenopyridine and hydroisoquinoline derivatives via the cleavage of a C-C bond under transition-metal-free conditions. This reaction provides facile access to complex nitrogen-containing heterocycles by simply mixing three common starting materials in EtOH in the presence of 20 mol % NaOH under microwave irradiation conditions.

Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction

An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.

Diastereoselective hydrogenation of substituted quinolines to enantiomerically pure decahydroquinolines

The stereoselective hydrogenation of auxiliary-substituted quinolines was used to build up saturated and partially saturated heterocycles. In a first step, the formation and diastereoselective hydrogenation of 2-oxazolidinone- substituted quinolines to 5,6,7,8-tetrahydroquinolines is reported. In this unprecedented process, stereocenters on the carbocyclic quinoline ring were formed with a dr of up to 89:11. Platinum oxide as a catalyst and trifluoroacetic acid as a solvent were found to be optimal for high levels of chemo- and stereoselectivity in this step. In a second hydrogenation step, the completely saturated decahydroquinolines with 4 newly formed stereocenters were obtained with enantioselectivities of up to 99%. Rhodium on carbon as a catalyst and acetic acid as a solvent gave the best results for this hydrogenation and allowed a traceless cleavage of the chiral auxiliary. Thus, this new method allows an efficient stereoselective synthesis of valuable 5,6,7,8-tetrahydro- and decahydroquinoline products.