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
• Article Data: 25

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

General Description

(E)-Ethyl 4-oxopent-2-enoate, also known as ethyl acetylacetate, is a chemical compound with the formula C6H10O3. It is a colorless liquid with a fruity, acetone-like odor, and is commonly used as a flavoring agent in the food and beverage industry. It is also utilized as a solvent in the production of pharmaceuticals and perfumes. Additionally, (E)-Ethyl 4-oxopent-2-enoate is an intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. It is considered to have low toxicity and is generally regarded as safe for use in consumer products when handled and stored appropriately.

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 
• 64-17-5 ethanol 
• 123-76-2 levulinic acid 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 116-09-6 hydroxy-2-propanone 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 924-44-7 glyoxylic acid ethyl ester 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 2833-28-5 trans-4-oxo-2-pentenoic acid 
• 126580-11-8 ethyl 2-diazo-3-methyl-3-butenoate 
• 1341127-67-0 ethyl 2-diazo-4-oxopentanoate 
• 93044-06-5 acetyl-succinic acid-4-ethyl ester-1-tert-butyl ester 

Downstream Products

• 145106-32-7 (E)-ethyl 4-((triisopropylsilyl)oxy)penta-2,4-dienoate 
• 102370-01-4 (+/-)-trans-6-acetyl-cyclohex-3-enecarboxylic acid 
• 1042450-60-1 (3S,4S)-ethyl 3-benzyl-6-methyl-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 352276-28-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol 
• 145667-75-0 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 1088105-31-0 (S)-ethyl 2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-4-oxopentanoate 

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.

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.

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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.

Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.