4553-07-5

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL PHENYLCYANOACETATE is used as a reagent for the asymmetric synthesis of (-)-manzacidin A, a potent antibiotic with potential applications in treating bacterial infections. Its role in this synthesis process is crucial, as it contributes to the development of new and effective treatments for various diseases.
Used in Chemical Synthesis:
ETHYL PHENYLCYANOACETATE is used as a useful reagent for C-C bond formation through conjugate additions with vinyl sulfones. This application is significant in the field of organic chemistry, as it enables the creation of new and complex molecular structures with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 576, 1942 DOI: 10.1021/ja01255a033Organic Syntheses, Coll. Vol. 4, p. 461, 1963Synthesis, p. 67, 1983

InChI:InChI=1/C11H11NO2/c1-2-14-11(13)10(8-12)9-6-4-3-5-7-9/h3-7,10H,2H2,1H3/t10-/m1/s1

Upstream product

• 140-29-4 phenylacetonitrile 
• 105-58-8 Diethyl carbonate 
• 26388-11-4 Natrium-phenylacetonitril 
• 6132-42-9 o-nitrophenyl ethyl carbonate 
• 108-86-1 bromobenzene 
• 105-56-6 ethyl 2-cyanoacetate 
• 591-50-4 iodobenzene 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 108-90-7 chlorobenzene 
• 12082-05-2 (η6-fluorobenzene)tricarbonylchromium 
• 65950-84-7 ethyl 2-cyano-2-diazoacetate 
• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 

Downstream Products

• 103097-83-2 2,2'-dicyano-2,2'-diphenyl-3,3'-piperazine-1,4-diyl-di-propionic acid diethyl ester 
• 101878-26-6 2-cyano-3-(2,6-dioxo-cyclohexyl)-2-phenyl-propionic acid methyl ester 
• 133905-22-3 2-cyano-2-phenyldiethyl glutarate 
• 83961-20-0 Phenyl-propyl-cyanessigsaeureethylester 
• 139882-33-0 cyano-phenyl-acetic acid-(2-hydroxy-ethylamide) 
• 52370-87-3 ethyl 5-chloro-2-cyano-2-phenylpentanoate 
• 66205-43-4 cyano-allyl-phenyl-acetic acid ethyl ester 
• 53555-70-7 2,4-dicyano-2-phenyl-butyric acid ethyl ester 
• 80544-83-8 cyano-phenyl-acetic acid anilide 
• 66205-41-2 ethyl 2-cyano-2-phenylhexanoate 
• 66205-44-5 ethyl 2-cyano-2-cyclohexyl-2-phenylacetate 
• 101583-01-1 2-cyano-2-phenyldiethyl adipate 
• 718-71-8 ethyl 2-cyano-2-phenylbutanoate 
• 2628-88-8 2-phenyl-1,6-hexanedioic acid 

Relevant academic research and scientific papers

Radical trifunctionalization of hexenenitrile via remote cyano migration

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken

Palladium(II)-catalyzed cross-coupling of diazo compounds and isocyanides to access ketenimines

Diazo compounds and isocyanides are reactive functionalities and valuable building blocks commonly utilized in organic synthesis. Their cross-coupling for the synthesis of useful isolable ketenimines remains an unsolved challenge in synthetic chemistry. Herein, we report a general method for the preparation of ketenimines via a palladium-catalyzed cross-coupling of easily accessible diazo compounds with isocyanides. The reaction benefits from the use of readily available starting materials, a wide substrate scope, high functional group tolerance, and a high yield in products, and the resultant ketenimines are amenable to further functionalization. Experimental findings and DFT calculations unambiguously corroborate the initial formation of a Pd(II)? isocyanide complex as the active catalytic species, which enables the cross-coupling reaction via a migratory insertion of Pd(II)? carbene into isocyanide, with evidence suggesting that the oxidation state of Pd(II) remains unchanged during the reaction.

Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel

A molecular shuttle consisting of a dibenzo-24-crown-8 macrocycle and an axle with two degenerate peripheral triazolium stations, a central dibenzyl ammonium station, and two anthracenes stoppers was exposed to 2-cyano-2-phenylpropanoic acid as a chemical fuel. Protonation/deprotonation of the amine reversibly switches the rotaxane from a static and little emissive to a dynamic fluorescent shuttling device, the latter exhibiting rapid motion (15 kHz at 25 °C). Four fuel cycles were run.

AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage

A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.

UV-mediated decomposition of diazomalonates in benzene: Unexpected access to functionalized bicyclo[3.2.0]heptane skeleton

Upon irradiation with 300-nm UV light, the photolysis of diazomalonates in benzene unexpectedly affords 2,6-dicarboxylate bicyclo[3.2.0]hepta-2,6-dienes in low yields. These products are proven to be derived from cyclohepta-1,3,5-triene intermediates presumably via a tandem 1,5-carboxylate migration/[2+2] cycloaddition sequence.

THIOAMIDES AND AMIDES FOR CONTROLLING ANIMAL PESTS

The invention relates to the use of a compound of formula (I) or a salt thereof for combating animal pests, where the symbols and indices are defined in the specification.

Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine

α-Arylated carbonyl derivatives are important structural motifs in many natural products and pharmaceutically active compounds. Although arylation of simple monocarbonyl compounds is a well-established methodology, metal-catalyzed arylation of β-dicarbonyl derivatives is significantly more challenging. The ability of β-dicarbonyl anions to bind to palladium in a κ2-O,O mode, rather than the κ1-C-bound mode required for bond formation, often results in the deactivation of catalyst systems. The C-bound form of the enolate can be favored through the use of sterically demanding ligands. Herein, we report that the sterically demanding di-tert-butylneopentylphosphine (DTBNpP) ligand in combination with Pd(dba)2 provides an effective catalyst for the coupling of aryl bromides and chlorides with diethyl malonate. The Pd/DTBNpP system also catalyzes the coupling of aryl bromides with ethyl cyanoacetate.

Synergistic effect of a bis(proazaphosphatrane) in mild palladium-catalyzed direct α-arylations of nitriles with aryl chlorides

The effect of a bis(proazaphosphatrane) ligand on the palladium-catalyzed direct α-arylation of nitriles with various aryl chlorides under mild conditions is reported. Comparisons of the catalytic properties of this ligand with those of three related mono(proazaphosphatrane)s under the same reaction conditions revealed that bis(proazaphosphatrane) displayed a synergistically enhanced activity. In the presence of the bis(proazaphosphatrane) ligand, ethyl cyanoacetate and primary as well as secondary nitriles were efficiently coupled with a wide variety of aryl chlorides that contained electron-rich, electron-poor, and electron-neutral groups.

Copper(I) enolate complexes in α-arylation reactions: Synthesis, reactivity, and mechanism

Copper is all bound up: The copper-catalyzed α-arylation of carbonyl compounds occurs through oxidative addition of iodoarenes to the C-bound Cu I enolate species 1 to form an aryl-CuIII intermediate (see scheme). Computational results provide insight into the origins of the relative reactivity of various CuI enolate complexes in the reactions with iodoarenes. Copyright

COMPOUNDS FOR THE REDUCTION OF β-AMYLOID PRODUCTION

The present disclosure provides a series of compounds of the formula (I), which modulate β-amyloid peptide (β-ΑΡ) production and are useful in the treatment of Alzheimer's Disease and other conditions affected by β-amyloid peptide (β-ΑΡ) production.