14274-07-8

Basic information

• Product Name: Methyl-4-oxo-4-phenyl-2-butenoate
• Synonyms: Methyl-4-oxo-4-phenyl-2-butenoate
• CAS NO: 14274-07-8
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.1953
• Mol File: 14274-07-8.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 289.5°Cat760mmHg
• Flash Point: 125.1°C
• Appearance: /
• Density: 1.134g/cm³
• Vapor Pressure: 0.0022mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: Methyl-4-oxo-4-phenyl-2-butenoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-4-oxo-4-phenyl-2-butenoate(14274-07-8)
• EPA Substance Registry System: Methyl-4-oxo-4-phenyl-2-butenoate(14274-07-8)

Safety Data

• Hazardous Substances Data: 14274-07-8(Hazardous Substances Data)

Usage

General Description

Methyl-4-oxo-4-phenyl-2-butenoate, also known as 4-oxo-4-phenyl-2-butenoic acid methyl ester, is a chemical compound with the molecular formula C11H10O3. It is a yellow solid with a fruity odor and is commonly used as a flavoring agent in food products. This chemical is also used in the production of pharmaceuticals and as an intermediate in organic synthesis. Methyl-4-oxo-4-phenyl-2-butenoate is known to be a potent inhibitor of the enzyme glyceraldehyde-3-phosphate dehydrogenase, and it has been studied for its potential anti-cancer and anti-inflammatory properties. However, it is important to handle this chemical with caution as it is flammable and may cause irritation to the skin, eyes, and respiratory system upon exposure.

InChI:InChI=1/C11H10O3/c1-14-11(13)8-7-10(12)9-5-3-2-4-6-9/h2-8H,1H3/b8-7+

Upstream product

• 71-43-2 benzene 
• 33553-90-1 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester 
• 121-44-8 triethylamine 
• 60-29-7 diethyl ether 
• 109-89-7 diethylamine 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 56015-01-1 methyl 4-hydroxy-4-phenyl-(E)-but-2-enoate 
• 100-58-3 phenylmagnesium bromide 
• 7327-99-3 4-oxo-but-2-enoic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 96-32-2 bromoacetic acid methyl ester 
• 98-86-2 acetophenone 
• 17812-07-6 Benzoylacrylic acid 

Downstream Products

• 101089-22-9 2-ethoxy-6-phenyl-3,4-dihydro-2H-pyran-4-carboxylic acid methyl ester 
• 715-19-5 2-Difluormethyl-phenyl-acrylsaeuremethylester 
• 77596-92-0 α-(4-Chlorbenzoyl)-γ-oxobenzolbutansaeure-methylester 
• 304887-56-7 2-nitromethyl-4-oxo-4-phenyl-butyric acid methyl ester 

Relevant articles and documents

Polarographic behavior of methyl 4-aryl-2,4-dioxobutanoates

Polarographic reduction of methyl 4-aryl-2,4-dioxobutanoates in aqueous 2-propanol involves two cathodic waves and yields methyl 4-aryl-2,4-dihydroxybutanoates.

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Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers

The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.

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.