10150-93-3

Basic information

• Product Name: (E)-Ethyl 4-oxopent-2-enoate
• Synonyms: (E)-Ethyl 4-oxopent-2-enoate;Ethyl (E)-4-oxopent-2-enoate;(E)-Ethyl 4-oxo-2-pentenoate;Ethyl trans-4-oxo-2-pentenoate;(2E)-4-Oxo-2-pentenoic acid ethyl ester
• CAS NO: 10150-93-3
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.1525
• Mol File: 10150-93-3.mol

Chemical Properties

• Boiling Point: 220.4 °C at 760 mmHg
• Flash Point: 89.5 °C
• Appearance: /
• Density: 1.027 g/cm³
• Vapor Pressure: 0.114mmHg at 25°C
• Refractive Index: 1.438
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (E)-Ethyl 4-oxopent-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-Ethyl 4-oxopent-2-enoate(10150-93-3)
• EPA Substance Registry System: (E)-Ethyl 4-oxopent-2-enoate(10150-93-3)

Safety Data

• Hazardous Substances Data: 10150-93-3(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Agents:
(E)-Ethyl 4-oxopent-2-enoate is used as a flavoring agent in the food and beverage industry, adding distinctive fruity notes to various products, enhancing their taste and aroma.
Used in Solvents:
In the pharmaceutical and perfume industries, (E)-Ethyl 4-oxopent-2-enoate serves as a solvent, facilitating the production process by dissolving and mixing various ingredients, which is essential for creating effective and stable formulations.
Used in Synthesis of Organic Compounds:
(E)-Ethyl 4-oxopent-2-enoate is utilized as an intermediate in the synthesis of a range of organic compounds, including pharmaceuticals and agrochemicals. Its role in these syntheses is crucial for the development of new and improved products in these fields.
Used in Consumer Products:
Considering its low toxicity and general safety for use in consumer products when handled and stored appropriately, (E)-Ethyl 4-oxopent-2-enoate contributes to the safety and quality of a variety of consumer goods, ensuring that they meet regulatory standards and consumer expectations.

InChI:InChI=1/C7H10O3/c1-3-10-7(9)5-4-6(2)8/h4-5H,3H2,1-2H3/b5-4+

Upstream product

• 539-88-8 4-oxopentanoic acid ethyl ester 
• 54397-57-8 2-oxo-but-3-ene-1,1,4t-tricarboxylic acid triethyl ester 
• 92252-64-7 Ethyl 3(R,S)-benzoyloxy-4-oxopentanoate 
• 924-44-7 glyoxylic acid ethyl ester 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 118346-70-6 (Z)-4-Oxo-2-pyrrolidin-1-yl-pent-2-enoic acid ethyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 78-98-8 2-oxopropanal 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 623-50-7 ethyl 2-hydroxyacetate 
• 64-17-5 ethanol 
• 123-76-2 levulinic acid 
• 95636-04-7 methyl-4 phenyl sulfonyl-2 pentene-4 oate d'ethyle 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 145106-32-7 (E)-ethyl 4-((triisopropylsilyl)oxy)penta-2,4-dienoate 
• 125048-94-4 C₆₄H₁₁₀O₁₃SSi₄ 
• 125024-35-3 C₆₅H₁₁₄O₁₄SSi₄ 
• 1042450-60-1 (3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate 
• 1397692-14-6 (6S,10S)-diethyl 4,8-dioxo-3-phenyl-2-thioxo-1-thia-3-azaspiro[4.5]decane-6,10-dicarboxylate 
• 1345962-90-4 ethyl 4-acetyl-2-benzyl-5-hydroxy-6-methylnicotinate 
• 1345962-91-5 ethyl 4-acetyl-5-hydroxy-6-methyl-2-phenethylnicotinate 
• 1345962-93-7 (E)-ethyl 4-acetyl-5-hydroxy-6-methyl-2-styrylnicotinate 
• 1345962-92-6 ethyl 4-acetyl-5-hydroxy-2-(4-methoxyphenethyl)-6-methylnicotinate 
• 1345962-94-8 ethyl 4-acetyl-5-hydroxy-2-(3-methoxyphenethyl)-6-methylnicotinate 
• 1345962-95-9 ethyl 4-acetyl-5-hydroxy-2-(2-methoxyphenethyl)-6-methylnicotinate 
• 1345962-55-1 4-acetyl-2-benzyl-5-hydroxy-6-methylnicotinic acid 
• 1345962-56-2 4-acetyl-5-hydroxy-6-methyl-2-phenethylnicotinic acid 
• 1345962-58-4 (E)-4-acetyl-5-hydroxy-6-methyl-2-styrylnicotinic acid 

Relevant articles and documents

Organocatalytic asymmetric friedel-crafts alkylation of indoles with simple α,β-unsaturated ketones

Figure presented The first general and highly enantioselective organocatalytic Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones has been accomplished. Central to these studies has been the identification of a new catalyst amine salt, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis.

A comparison of Wittig and Wittig Horner (wadsworth emmons) reagents in reactions with some α-dicarbonyl compounds

For the α-dicarbonyl compounds RCOCHO studied where R=H, Me or Ph it was found that the use of Wittig reagents resulted in higher overall yields of the expected products and that with neither type of reagent could the product OCHCH=CHCO2Et from glyoxal be isolated.

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α-Hydroxyketones undergo efficient tandem oxidation-Wittig olefination reactions in the presence of an oxidant to produce high yields of γ-ketocrotonate products. On carrying out the oxidation-Wittig olefination reaction in the presence of 2,3-dimethyl-1,3-butadiene, a novel multicomponent reaction sequence provides access to cycloadducts in high yield.

Revisiting Bromohexitols as a Novel Class of Microenvironment-Activated Prodrugs for Cancer Therapy

Bromohexitols represent a potent class of DNA-alkylating carbohydrate chemotherapeutics that has been largely ignored over the last decades due to safety concerns. The limited structure?activity relationship data available reveals significant changes in cytotoxicity with even subtle changes in stereochemistry. However, no attempts have been made to improve the therapeutic window by rational drug design or by using a prodrug approach to exploit differences between tumour physiology and healthy tissue, such as acidic extracellular pH and hypoxia. Herein, we report the photochemical synthesis of highly substituted endoperoxides as key precursors for dibromohexitol derivatives and investigate their use as microenvironment-activated prodrugs for targeting cancer cells. One endoperoxide was identified to have a marked increased activity under hypoxic and low pH conditions, indicating that endoperoxides may serve as microenvironment-activated prodrugs.

A Regioselective Synthesis of 8,10-Dideoxycarminomycinone

A carminomycinone derivative has been synthesised from 5-hydroxyquinizarin and 2-methoxy-5-methyl-4-nitromethyltetrahydrofuran.

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.

Synthesis of pyrrolidine-3-carboxylic acid derivatives: Via asymmetric Michael addition reactions of carboxylate-substituted enones

To concisely synthesize highly enantiomerically enriched 5-alkyl-substituted pyrrolidine-3-carboxylic acids, organocatalytic enantioselective Michael addition reactions of 4-alkyl-substituted 4-oxo-2-enoates with nitroalkanes have been developed. Using the developed reaction method, 5-methylpyrrolidine-3-carboxylic acid with 97% ee was obtained in two steps.

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

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