49744-93-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a chemical intermediate for the synthesis of various drugs. Its unique cyano-phenyl moiety allows for the creation of a wide range of pharmaceutical compounds with different therapeutic properties.
Used in Research Laboratories:
3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is utilized in research laboratories for the development and testing of new organic compounds and pharmaceuticals. Its versatility and reactivity make it a valuable tool for chemists and researchers in the field of organic chemistry and drug discovery.
Used in Organic Compounds Synthesis:
3-(4-CYANO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a key component in the synthesis of various organic compounds. Its cyano-phenyl group can be further modified or reacted with other molecules to create new compounds with specific properties and applications.

InChI:InChI=1/C12H11NO3/c1-2-16-12(15)7-11(14)10-5-3-9(8-13)4-6-10/h3-6H,2,7H2,1H3

Upstream product

• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 141-78-6 ethyl acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 105-07-7 4-cyanobenzaldehyde 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 105-58-8 Diethyl carbonate 
• 64-17-5 ethanol 
• 619-65-8 4-cyanobenzoic Acid 
• 141-97-9 ethyl acetoacetate 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 623-03-0 4-Cyanochlorobenzene 
• 6148-64-7 ethyl potassium malonate 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 83204-56-2 4-(7-methoxy-2-oxo-2H-chromene-3-carbonyl)benzonitrile 
• 83179-55-9 3-(4-cyanobenzoyl)-5,7-dimethoxycoumarin 
• 77031-63-1 3-(4-cyanobenzoyl)coumarin 
• 98305-78-3 4-(2-Amino-6-oxo-1,6-dihydro-pyrimidin-4-yl)-benzonitrile 
• 252904-70-4 Ethyl 4-(4-cyanophenyl)-2-({2-[(4-methyl-5-nitro(2-pyridyl))amino]ethyl}amino)pyrimidine-5-carboxylate 
• 252904-43-1 Ethyl 2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}-amino)-4-(4-cyanophenyl)pyrimidine-5-carboxylate 
• 252904-45-3 4-(4-cyanophenyl)-2-[2-(5-nitropyridin-2-ylamino)ethylamino]pyrimidine-5-carboxylic acid ethyl ester 
• 252904-75-9 Ethyl 4-(4-cyanophenyl)-2-[(2-{[5-(trifluoromethyl) (2-pyridyl)]amino}ethyl)amino]pyrimidine-5-carboxylate 
• 252942-29-3 ethyl 2-(4-cyanophenyl)-6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyridine-3-carboxylate 
• 1088254-33-4 C₂₁H₂₄N₂O₃S 

Relevant academic research and scientific papers

Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products

A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.

Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles

An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition,

Amide/Ester Cross-Coupling via C-N/C-H Bond Cleavage: Synthesis of β-Ketoesters

Activated primary, secondary, and tertiary amides were coupled with enolizable esters in the presence of LiHMDS to obtain good yields of β-ketoesters at room temperature. Notably, this protocol provides an efficient, mild, and high chemoselectivity method

Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Desymmetrization of meso-dicarbonatecyclohexene with β-Hydrazino carboxylic esters via a Pd-catalyzed allylic substitution cascade

The desymmetrization of meso-dicarbonatecyclohexene with β-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction of chiral hexahydrocinnoline derivatives with high performance. Mechanistic studies reveal that the reaction exploits a pathway different from that of our previous work and that the first nitrogen nucleophilic process is the rate-determining step. The protocol could be conducted on a gram scale without any loss of catalytic behavior, and the corresponding chiral hexahydrocinnolines can undergo diverse transformations.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.

Bromide-Mediated C-H Bond Functionalization: Intermolecular Annulation of Phenylethanone Derivatives with Alkynes for the Synthesis of 1-Naphthols

Bromide-mediated intermolecular annulation of phenylethanone derivatives with alkynes has been developed, which allows for the regioselective formation of polysubstituted 1-naphthols. The usage of readily available bromine catalyst, broad substrate scope, and mild conditions make this protocol very practical. Mechanistic investigations reveal that the bromination of phenylethanone derivatives occurs to yield bromo-substituted intermediates, which react in situ with alkynes to furnish the desired 1-naphthols.

Regioselective Synthesis of Dihydrothiophenes and Thiophenes via the Rhodium-Catalyzed Transannulation of 1,2,3-Thiadiazoles with Alkenes

A method for the regioselective synthesis of a wide range of dihydrothiophenes was developed from the rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with aliphatic, aromatic, and heteroaromatic alkenes. Tandem rhodium-catalyzed transannulation of 1,2,3-thiadiazoles with alkenes followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation was also demonstrated for the one-pot regioselective synthesis of various thiophenes. Advantages of the present method include a broad substrate scope, wide functional group compatibility, and high regioselectivity.

1,5-Diketones Synthesis via Three-Component Cascade Reaction

A mild and efficient cascade synthesis of 1,5-diketones from readily available N,N-dicyclohexylmethylamine, 1,3-dicarbonyl compounds, and trifluoromethyl β-diketones has been developed. This cascade reaction occurs via an oxidation/Mannich reaction/Cope elimination/Michael addition/retro-Claisen reaction sequence, and provides multiple C-C bond formations in one pot. In addition, exquisite chemoselectivity is achieved in the reaction between 1,3-dicarbonyl compounds and trifluoromethyl β-diketones.

A palladium-catalyzed carbonylative-deacetylative sequence to 1,3-Keto Amides

An efficient three-component reaction involving carbon monoxide with a range of aryl bromides and N-substituted acetoacetamides is reported for the synthesis of b-keto amides. This transformation is promoted by Pd-catalysis followed by an acid-mediated deacetylation upon work-up, enabling a large number of b-keto amides to be isolated. Finally, d2-13C-dyclonine could be synthesized in three steps utilizing the developed catalytic system as the key step.