107969-78-8

Basic information

• Product Name: 3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)-
• CAS NO: 107969-78-8
• Molecular Formula: C11H10O3
• Molecular Weight: 190.199
• Mol File: 107969-78-8.mol

Chemical Properties

• CAS DataBase Reference: 3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)-(107969-78-8)
• EPA Substance Registry System: 3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)-(107969-78-8)

Safety Data

• Hazardous Substances Data: 107969-78-8(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Flavor Industry:
3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)is used as a synthetic oil in the fragrance and flavor industry for its sweet, fruity scent reminiscent of cinnamon.
Used in Perfume Production:
3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)is used as a key ingredient in the production of perfumes, contributing to their sweet and balsamic aroma.
Used in Soap and Detergent Industry:
3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)is used in the soap and detergent industry to impart a pleasant scent and enhance the sensory experience of the products.
Used in Pharmaceutical Industry:
3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)has potential applications in the pharmaceutical industry due to its antimicrobial properties, making it a promising candidate for the development of new antimicrobial agents.
Used in Agrochemical Industry:
3-Butenoic acid, 2-oxo-4-phenyl-, methyl ester, (3E)also has potential applications in the agrochemical industry, as its insecticidal properties can be utilized for the development of new pest control solutions.

Upstream product

• 67-56-1 methanol 
• 17451-19-3 benzylidene pyruvic acid 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 87352-10-1 N-methyl-5-carbomethoxy-3-phenyl-4,5-dehydroisoxazolidine 
• 87352-09-8 N-tert-butyl-3-phenyl-4,5-dehydro-5-carbomethoxyisoxazolidine 
• 600-22-6 pyruvic acid methyl ester 
• 100-52-7 benzaldehyde 
• 3947-97-5 3-phenyl-3-cyclobutene-1,2-dione 
• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 127-17-3 2-oxo-propionic acid 
• 112068-21-0 rac-(E)-2-hydroxy-4-phenyl-3-butenoic acid methyl ester 
• 118806-93-2 2-oxo-4-phenylbut-3-enoic acid potassium salt 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 1172623-45-8 (4S,4aR,8aR)-8a-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-phenyl-4a,5,6,7,8,8a-hexahydro-4H-chromene-2-carboxylic acid methyl ester 
• 1206901-02-1 C₁₉H₂₀N₂O₄ 
• 1206901-01-0 C₂₁H₁₈N₂O₃ 
• 1206900-97-1 C₁₆H₁₅NO₄ 
• 1206900-98-2 C₁₆H₁₇NO₄ 
• 1206901-03-2 C₁₇H₁₄F₃NO₄ 
• 1206901-08-7 C₂₆H₂₀N₂O₃ 
• 1228393-52-9 1,1-diisopropyl 4-methyl 4-oxo-2-phenylbutane-1,1,4-tricarboxylate 
• 1228393-53-0 1,1-di-tert-butyl 4-methyl 4-oxo-2-phenylbutane-1,1,4-tricarboxylate 

Relevant articles and documents

Interaction of hydroxylamine with esters of 2-oxobutenoic acids. Synthesis of 1-hydroxy-3-hydroximino-2-pyrrolidinones

New 3-hydroximino-1-hydroxy-2-pyrrolidinones have been synthesized by the interaction of NH2OH and NH2OBn with the methyl esters of 2-oxo-3-butenoic acid derivatives. Some intermediate compounds have been isolated and identified and

Stereo- and Regioselective [3+3] Annulation Reaction Catalyzed by Ytterbium: Synthesis of Bicyclic 1,4-Dihydropyridines

An ytterbium catalyzed formal [3+3] cycloaddition of cyclic enamines and α,β-unsaturated ketones catalyzed is reported. The reaction proceeds with a ‘head to tail’ regioselectivity through a conjugate addition of the enamine moiety followed by an amine-carbonyl condensation. In addition the use of chiral enamines provided a high degree of stereoselectivity, driven by a possible balance between steric and π-stacking effects. The resulting bicyclic 1,4-dihydropyridines were evaluated as antiproliferative agents against A549 (carcinomic human alveolar basal epithelial cell) and SKOV3 (human ovarian carcinoma) human tumor cell lines. Good toxicities were found for some of the compounds against A549 and SKOV3 cell lines, with best IC50 values of 0.89 μM for A549 and 6.69 μM for SKOV3, and a very good selectivity was observed towards MRC5 (non-malignant) cell lines. (Figure presented.).

Asymmetric Construction of α-Substituted β-Hydroxy Lactones via Ni Catalyzed Decarboxylative Addition Reaction

We described a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction of 2-oxotetrahydrofuran-3-carboxylic acid/2-oxochromane-3-carboxylic acid derivatives with different kinds of carbonyls. Under optimal reaction conditions, α-substituted β-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter have been generated with high levels of functional-group compatibility. Furthermore, proficient transformations of products were also described, in which an aliphatic tertiary alcohol and a multi-substituted 1,4-diol were smoothly constructed through hydrogenation and ring-opening reaction, respectively.

A Heck reaction/photochemical alkene isomerization sequence to prepare functionalized quinolines

A route to prepare functionalized quinolines based on a Heck reaction/UV-induced alkene isomerization sequence is described. The method allows for the preparation of quinolines under mild and neutral conditions and has broad functional group tolerance. Acid-sensitive functional groups that would not be tolerated under previous approaches can be included and a one-pot quinoline forming procedure is also reported.

Asymmetric Catalytic Formal 1,4-Allylation of β,γ-Unsaturated α-Ketoesters: Allylboration/Oxy-Cope Rearrangement

A highly enantioselective formal conjugate allyl addition of allylboronic acids to β,γ-unsaturated α-ketoesters has been realized by employing a chiral NiII/N,N′-dioxide complex as the catalyst. This transformation proceeds by an allylboration/oxy-Cope rearrangement sequence, providing a facile and rapid route to γ-allyl-α-ketoesters with moderate to good yields (65–92 %) and excellent ee values (90–99 % ee). The isolation of 1,2-allylboration products provided insight into the mechanism of the subsequent oxy-Cope rearrangement reaction: substrate-induced chiral transfer and a chiral Lewis acid accelerated process. Based on the experimental investigations and DFT calculations, a rare boatlike transition-state model is proposed as the origin of high chirality transfer during the oxy-Cope rearrangement.

Direct Synthesis of β,γ-Unsaturated α-Keto Esters from Aldehydes and Pyruvates

Herein, we describe two practical methods to synthesize β,γ-unsaturated α-keto esters directly from aldehydes and pyruvates promoted by BF 3 ?Et 2 O in the presence of Ac 2 O or by Ti(OEt) 4 under mild condition

Facile synthesis of substituted diaryl sulfones: Via a [3 + 3] benzannulation strategy

A base-mediated [3 + 3] benzannulation strategy for the conversion of 1,3-bis(sulfonyl)propenes and β,γ-unsaturated α-ketoesters to diaryl sulfones has been developed. This method provides facile, metal-free and efficient access to highly substituted diaryl sulfones in good to excellent yields. In addition, the sulfonyl group could be easily removed or converted to other functional groups via an organostannane intermediate.

A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides

A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.

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.

Boosting Chemical Stability, Catalytic Activity, and Enantioselectivity of Metal-Organic Frameworks for Batch and Flow Reactions

A key challenge in heterogeneous catalysis is the design and synthesis of heterogeneous catalysts featuring high catalytic activity, selectivity, and recyclability. Here we demonstrate that high-performance heterogeneous asymmetric catalysts can be engineered from a metal-organic framework (MOF) platform by using a ligand design strategy. Three porous chiral MOFs with the framework formula [Mn2L(H2O)2] are prepared from enantiopure phosphono-carboxylate ligands of 1,1′-biphenol that are functionalized with 3,5-bis(trifluoromethyl)-, bismethyl-, and bisfluoro-phenyl substituents at the 3,3′-position. For the first time, we show that not only chemical stability but also catalytic activity and stereoselectivity of the MOFs can be tuned by modifying the ligand structures. Particularly, the MOF incorporated with -CF3 groups on the pore walls exhibits enhanced tolerance to water, weak acid, and base compared with the MOFs with -F and -Me groups. Under both batch and flow reaction systems, the CF3-containing MOF demonstrated excellent reactivity, selectivity, and recyclability, affording high yields and enantioselectivities for alkylations of indoles and pyrrole with a range of ketoesters or nitroalkenes. In contrast, the corresponding homogeneous catalysts gave low enantioselectivity in catalyzing the tested reactions.