131504-53-5

Upstream product

• 4974-57-6 4-nitrophenylglyoxal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 924-44-7 glyoxylic acid ethyl ester 
• 1439-43-6 1-(4-nitro-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 64-17-5 ethanol 
• 63104-97-2 (E)-4-(4-nitrophenyl)-4-oxobut-2-enoic acid 
• 100-19-6 (4-nitrophenyl)ethanone 
• 99-81-0 4-Nitrophenacyl bromide 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 17730-93-7 (4'-nitrophenacyl)triphenylphosphonium bromide 

Downstream Products

• 1283748-98-0 ethyl 3-chloro-2-(4-methylphenylsulfonamido)-4-(4-nitrophenyl)-4-oxobutanoate 
• 1383731-12-1 (Z)-ethyl 4-((diphenoxyphosphoryl)oxy)-4-(4-nitrophenyl)but-3-enoate 
• 1107060-59-2 1-(4-nitrobenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester 
• 1185984-63-7 ethyl (R)-2-(nitromethyl)-4-(4-nitrophenyl)-4-oxobutanoate 
• 1360110-61-7 (2S,3S,4S)-tert-butyl 2-ethyl 3-(4-nitrobenzoyl)-4-(2-oxoethyl)-3,4-dihydro-1H-carbazole-2,9(2H)-dicarboxylate 

Relevant academic research and scientific papers

Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines

The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study

Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.

Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives

Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps. (Chemical Equation Presented).

Enantioselective conjugate addition of aliphatic thiols to divergently activated electron poor alkenes and dienes

Divergently activated double bonds in electron poor 4-oxo-butenoates and (2E,4E)-6-oxo-2,4-dienoates underwent stereoselective and regioselective addition of mercaptans catalyzed by simple Cinchona alkaloids. Application of quinine and quinidine afforded both enantiomers of the 1,4-adducts with respect to the ketone carbonyl group in ees of up to 80%. Single recrystallization of some adducts resulted in further enrichment of up to 99%ee.

Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates

A useful Michael addition reaction using nitroalkanes as the nucleophile and 4-oxo-enoates as the Michael acceptor has been disclosed, and the reaction allows expedient access to functionalized chiral γ-keto esters in high yields and excellent enantioselectivities (up to 98% ee), with a low catalyst loading.

Design, synthesis and conformational analysis of turn inducer cyclopropane scaffolds: microwave assisted amidation of unactivated esters on catalytic solid support to obtain γ-turn mimic scaffolds

Novel constrained 1-aroyl-cyclopropane-2,3-cis-dicarboxylic acid bis-[(2-hydroxy-ethyl)-amides] (17a-e) with varied torsional angles have been synthesized in high yield from unactivated esters of 1-aroyl-2,3-cis-diethoxycarbonylcyclopropanes (15a-e) on a catalytic solid support with reduced reaction times by using the monomode-microwave irradiation; 15a-e were obtained by diastereoselective ethoxycarbonylmethylene transfer from a sulfur ylide to ethyl β-aroylacrylates (10a-e). Torsional angles and interatomic distance measurements on the energy minimized structures of the obtained molecules (17a-e, DFT, B3LYP/6-31G* level) have established these molecules as valuable γ-turn mimic scaffolds.

Process for preparing trans-β-aroylacrylic ester

A process for preparing a trans-β-aroylacrylic ester which comprises reacting an aryl methyl ketone and an alkyl acetal of alkyl glyoxylate in the presence of an acid catalyst with heating. This process is excellent in operability, safety and ecomony and therefore is industrially advantageous process.