80937-23-1

Usage

Uses

Used in Pharmaceutical Research:
(E)-Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate is used as a potential drug candidate in pharmaceutical research for its potential anti-inflammatory and anti-cancer properties. It is being studied for its ability to modulate biological pathways associated with inflammation and cancer, offering a promising avenue for the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (E)-Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate serves as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for creating a range of chemical products.
Used in Agrochemical Development:
(E)-Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate is also being investigated for its potential application in the development of herbicides and insecticides. Its chemical properties may contribute to the creation of novel agrochemicals that can effectively control pests and weeds, thereby enhancing crop protection and yield.
Used in Scientific Research:
Across various scientific fields, (E)-Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate is used as a subject of study to explore its chemical properties, reactivity, and potential applications. Researchers are interested in understanding its behavior in different chemical reactions and environments, which can lead to the discovery of new uses and applications for (E)-Ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate.

InChI:InChI=1/C14H16O5/c1-4-19-14(16)8-6-11(15)10-5-7-12(17-2)13(9-10)18-3/h5-9H,4H2,1-3H3/b8-6+

Upstream product

• 108-31-6 maleic anhydride 
• 91-16-7 1,2-dimethoxybenzene 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 563-96-2 2,2-dihydroxyacetic acid 
• 89781-43-1 ethyl (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate 
• 298-12-4 Glyoxilic acid 
• 127172-22-9 1-(3,4-dimethoxyphenyl)-3-(dimethylamino)prop-2-en-1-one 

Downstream Products

• 80937-21-9 (E)-methyl 4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoate 
• 89781-43-1 ethyl (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate 
• 117379-57-4 (E)-4-(3,4-dimethoxyphenyl)-4-hydroxy-2-butenoic acid 
• 117379-59-6 (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenohydroxamic acid 
• 79841-69-3 C₁₄H₁₄O₆ 
• 128934-99-6 5-(3,4-dimethoxyphenyl)furan-2(5H)-one 
• 117379-60-9 (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenamide 

Relevant academic research and scientific papers

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans

A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.

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.

Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents

The invention discloses application of a 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents. The structure of the 4-oxo-2-crotonamide derivative is shown as a formula (I). The 4-oxo-2-crotonamide derivative has a bacteriostatic effect; good antibacterial activity can be realized on methicillin-resistant staphylococcus aureus, methicillin-resistant staphylococcus epidermidis, vancomycin drug-resistant enterococcus faecalis, vancomycin drug-resistant enterococcus faecium, methicillin-sensitive staphylococcus aureus, methicillin-sensitive staphylococcus epidermidis, vancomycin-sensitive enterococcus faecalis and vancomycin-sensitive enterococcus faecium. The formula I is shown in the description.

An efficient synthesis of β-Aroylacrylic acid ethyl ester by the Friedel-Crafts reaction in the presence of diethyl sulfate

An β-Aroylacrylic acid ethyl ester such as ethyl (E)-4-(3,4- dimethoxyphenyl)-4-oxo-2-butenoate (1) can be obtained in good yield and with excellent purity by way of the Friedel-Crafts reaction in which 1,2-dimethoxybenzene (2) is treated with maleic anhydride (3) and aluminum chloride in the presence of diethyl sulfate (4) under mild conditions. Copyright

PROCESS FOR PRODUCING 4-PHENYL-4-OXO-2-BUTENOIC ESTER DERIVATIVE

A 4-phenyl-4-oxo-2-butenoate derivative is stably supplied in a short period of time, at low cost, in high purity and on an industrial scale by a process for producing the 4-phenyl-4-oxo-2-butenoate derivative, which comprises simultaneously or continuously reacting a sulfuric ester, an aromatic hydrocarbon and a maleic anhydride derivative.

Synthetic Studies on O-Heterocycles via Cycloadditions. Part 2. Adducts from Styrene Oxides

The styrene oxides (14) and (15), bearing electron-withdrawing functions, readily undergo thermal and photochemical (triplet sensitised) dipolar cycloadditions with simple electron-deficient olefins, regioselectively in the case of methyl acrylate.However, cycloadditions with 5-arylbutenolides as dipolarophiles, required for lignan synthesis, could not be effected in significant yield.A new short route to 5-arylbut-2-enolides was devised.The dihydro- and tetrahydro-furan adducts (18d), (19d), and (20d) all fragment in base to the dienol nitrile (25).

Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids

A class of anti-secretory, anti-ulcer and cytoprotective agents, the substituted (E)-4-phenyl and heteroaryl-4-oxo-2-butenoic acids, is described.This chemical structure is not related to those of any known anti-cholinergic drugs, histamine H2-receptor antagonists or prostaglandins.Five compounds, 4-(2-methoxyphenyl)- 15, 4-(4-methoxyphenyl)- 22, 4-(3,4-dimethoxyphenyl)- 32, 4-(3,4,5-trimethoxyphenyl)- 40, and 4-(2-furanyl)-4-oxo-2-butenoic acid 44, have cytoprotective activity at a very low dose (0.6 mg/kg, p.o.) and anti-secretory and anti-ulcer activities at higher doses.One of these compounds, RU 38086 40, has been selected for clinical evaluation.Keywords - anti-ulcer agents / cytoprotective agents / (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids.

3-benzoyl-2-mercaptopropionic acid derivatives

3-Benzoyl-2-mercaptopropionic acid derivatives represented by the general formula STR1 (wherein, X represents a hydrogen atom, a halogen atom, hydroxy group, a lower alkyl group or a lower alkoxy group, Y represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, Z represents a hydrogen atom or an acyl group, and R represents a hydrogen atom or a lower alkyl group). These compounds have immunomodulative function and are effective for the treatment of diseases caused by abnormal immunofunction.

Gastro-protecting activity

Diseases and ailments accompanied by gastric and gastroduodenal lesions treated by administering a compound of the formula (I) STR1 in which R represents hydrogen or alkyl containing 1 to 5 carbon atoms and R1 and R2, identical or different, both represent alkoxy containing 1 to 3 carbon atoms, or both represent halogen, or R1 represents hydrogen and R2 represents halogen, nitro or trifluoromethyl, or R1 and R2 form a methylenedioxy group at adjacent carbon atoms, as well as pharmaceutically acceptable salts thereof, particularly alkali metal, alkaline earth metal, or amine salts of said acid.