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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 that exhibits a fruity odor and is recognized for its diverse applications in the food, pharmaceutical, and chemical industries.

14274-07-8

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14274-07-8 Usage

Uses

Used in Flavoring Industry:
Methyl-4-oxo-4-phenyl-2-butenoate is used as a flavoring agent for its fruity aroma, enhancing the taste and appeal of various food products.
Used in Pharmaceutical Industry:
Methyl-4-oxo-4-phenyl-2-butenoate is utilized in the production of pharmaceuticals, capitalizing on its potential anti-cancer and anti-inflammatory properties. It acts as a potent inhibitor of the enzyme glyceraldehyde-3-phosphate dehydrogenase, which is implicated in various disease processes.
Used in Organic Synthesis:
This chemical compound serves as an intermediate in organic synthesis, facilitating the creation of other complex organic molecules for a range of applications.
Safety Considerations:
It is crucial to handle Methyl-4-oxo-4-phenyl-2-butenoate with care due to its flammable nature and potential to cause irritation to the skin, eyes, and respiratory system upon exposure. Proper safety measures should be implemented during its use in various industries.

Check Digit Verification of cas no

The CAS Registry Mumber 14274-07-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,7 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14274-07:
(7*1)+(6*4)+(5*2)+(4*7)+(3*4)+(2*0)+(1*7)=88
88 % 10 = 8
So 14274-07-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H10O3/c1-14-11(13)8-7-10(12)9-5-3-2-4-6-9/h2-8H,1H3/b8-7+

14274-07-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl (E)-4-oxo-4-phenylbut-2-enoate

1.2 Other means of identification

Product number -
Other names methyl trans-4-oxo-4-phenylbut-2-enoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14274-07-8 SDS

14274-07-8Relevant articles and documents

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

Posyagin,Posyagina,Zalesov,Kataev

, p. 1574 - 1577 (2001)

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.

Organic base-catalyzed stereoselective isomerizations of 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester to (E)- and (Z)-4-oxo-4-phenyl-but-2-enoic acid methyl esters

Sonye, John P.,Koide, Kazunori

, p. 599 - 602 (2006)

We have developed a 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed isomerization of 4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester to (E)-4-oxo-4-phenyl-but-2-enoic acid methyl ester and an N,N- diisopropylethylamine-catalyzed isomerization of the same

On the mechanism of DABCO-catalyzed isomerization of γ-hydroxy- α,β-alkynoates to γ-oxo-α,β(E)-alkenoates

Sonye, John P.,Koide, Kazunori

, p. 199 - 202 (2006)

Since the discovery of organic base-catalyzed isomerization of γ-hydroxy-α,β-acetylenic esters to γ-oxo-α,β- trans-alkenyl esters in 1949, the mechanism has not been elucidated. This study shows that the mechanism involves cumulene formation, protonation

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

Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 1611 - 1615 (2021/03/03)

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.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He

, p. 4327 - 4337 (2021/05/31)

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

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

De Bruin, Bas,De Zwart, Felix J.,Li, Zirui,Mathew, Simon,Wolzak, Lukas A.,Zhou, Minghui

, p. 20501 - 20512 (2021/12/03)

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.

Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation

Guo, Kai,Huang, Jun,Li, Anding,Li, Yuanhe,Yang, Zhen,Zhang, Zhongchao

supporting information, p. 11660 - 11668 (2020/05/25)

Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

Ren, Jinfeng,Xu, Jian,Zhang, Guoning,Xu, Changliang,Zhao, LiLi,You, XueFu,Wang, Yucheng,Lu, Yu,Yu, Liyan,Wang, Juxian

, p. 539 - 543 (2019/01/09)

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.

A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water

Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen

supporting information, p. 5074 - 5077 (2018/05/26)

A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.

α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones

Gallo, Rafael D. C.,Ahmad, Anees,Metzker, Gustavo,Burtoloso, Antonio C. B.

, p. 16980 - 16984 (2017/11/27)

A one-pot alkylation–halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.

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