35338-15-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE is used as an intermediate in the pharmaceutical industry for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows it to serve as a building block in the creation of complex molecules with potential therapeutic properties.
Used in Organic Chemistry:
In the field of organic chemistry, (E)-ETHYL 4-(4-BROMOPHENYL)-4-OXOBUT-2-ENOATE is utilized as a versatile intermediate for the development of new organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of a wide range of chemical products.
Safety Precautions:

InChI:InChI=1/C12H11BrO3/c1-2-16-12(15)8-7-11(14)9-3-5-10(13)6-4-9/h3-8H,2H2,1H3/b8-7+

Upstream product

• 5195-29-9 4-bromophenylglyoxal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 64-17-5 ethanol 
• 20972-38-7 (E)-4-(4-bromophenyl)-4-oxobut-2-enoic acid 
• 924-44-7 glyoxylic acid ethyl ester 
• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 
• 99-90-1 para-bromoacetophenone 
• 1071-46-1 hydrogen ethyl malonate 
• 99-73-0 para-bromophenacyl bromide 
• 2928-58-7 (2-oxo-2-p-bromophenylethyl)triphenylphosphonium bromide 
• 108-86-1 bromobenzene 
• 39644-80-9 β-(4-bromobenzoyl)acrylic acid 
• 35497-00-8 Triphenyl-β-keto-p-bromphenylphosphonium 
• 117937-01-6 4-(4-bromophenyl)-4-hydroxybut-2-ynoic acid ethyl ester 

Downstream Products

• 1107060-58-1 1-(4-bromobenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester 
• 1042450-48-5 (R)-ethyl 6-(4-bromophenyl)-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate 
• 1116119-11-9 C₂₀H₁₈BrNO₃ 
• 1116119-20-0 C₂₀H₁₇Br₂NO₃ 
• 1185984-94-4 ethyl (R)-4-(4-bromophenyl)-2-(nitromethyl)-4-oxobutanoate 
• 30913-87-2 4-(4-bromophenyl)-4-oxobutanoic acid ethyl ester 
• 1253050-37-1 C₁₃H₁₄BrNO₅ 

Relevant academic research and scientific papers

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.

Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions

Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).

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.

Base-Controlled Reactions through an Aldol Intermediate Formed between 2-Oxoaldehydes and Malonate Half Esters

A practical, atom-economical, base-directed, and highly efficient method for the generation of different selective products through a common aldol intermediate of 2-oxoaldehydes and malonate half esters is successfully developed. The addition of a strong basic environment (potassium tert-butoxide) catalyzed the synthesis of stable decarboxylative aldol products (α-hydroxy ketones), while the Doebner modification procedure resulted in decarboxylative elimination to (E)-α,β-unsaturated esters in good yields. The application of this method in one pot and one pot/two steps with azoles helped to develop regioselective α- and β-azolated products in appreciable yields.

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).

Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst

A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.

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.

Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents

Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright

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.