14025-79-7

Usage

InChI:InChI=1/C9H7NO2/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8H,(H,11,12)

Upstream product

• 153463-68-4 2-Cyano-1-hydroxy-2-phenyl-ethenol anion 
• 140-29-4 phenylacetonitrile 
• 585-34-2 3-tert-butylphenyol 
• 58425-32-4 potassium m-t-butylphenate 
• 124-38-9 carbon dioxide 
• 4553-07-5 ethyl phenylcyanoacetate 
• 15719-64-9 methylammonium carbonate 

Downstream Products

• 30698-30-7 methyl 2-cyano-2-phenylacetate 
• 124-38-9 carbon dioxide 
• 140-29-4 phenylacetonitrile 
• 69606-54-8 α-cyano-phenylacetic acid pentachlorophenyl ester 
• 69606-55-9 α-cyano-phenylacetic acid pentafluorophenyl ester 
• 91012-17-8 (+/-)-methyl 3-amino-2-phenylpropanoate hydrochloride 
• 4370-95-0 3-amino-2-phenyl-propionic acid 
• 153463-68-4 2-Cyano-1-hydroxy-2-phenyl-ethenol anion 

Relevant academic research and scientific papers

Carboxylation of Active Methylene Compounds Using Anilide, Potassium Carbonate, and Carbon Dioxide

Active methylene compounds were effectively carboxylated with carbon dioxide in the presence of anilide (acetanilide or formanilide) and potassium carbonate at 20-40 deg C for 0.5-10 h.In the carboxylation of fluorene, a high yield (48percent) was obtained at 20 deg C for 4 h.The yield of carboxylic acid using 2,6-dimethylacetanilide was 8.9percent, and smaller than 26.6percent when using acetanilide at 20 deg C for 2 h, indicating the interference of a methyl group for the carboxylation.

The Carboxylation of Active Methylene Compounds with Carbon Dioxide in the Presence of 18-Crown-6 and Potassium Carbonate

Active methylene compounds were carboxylated with the reagent system, 18-crown-6, potassium carbonate and carbon dioxide, in dimethyl sulfoxide at room temperature and atmospheric pressure.The concentration of the carbonate ion is important for carboxylation.

Decarboxylative benzylation and arylation of nitriles

Decarboxylative benzylation of nitriles is achieved via coupling of metallated nitriles with Pd-π-benzyl complexes that are generated in situ from cyanoacetic benzyl esters. In addition, decarboxylative couplings of α,α-disubstituted 2-methylfuranyl cyano

Regiospecific decarboxylative allylation of nitriles

[Chemical Equation Presented] Palladium-catalyzed decarboxylative α-allylation of nitriles readily occurs with use of Pd2(dba) 3 and rac-BINAP. This catalyst mixture also allows the highly regiospecific α-allylation of nitriles in the presence of much more acidic α-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.

The α-Cyano-α-phenylacetic acid keto-enol system. Flash photolytic generation of the enol in aqueous solution and determination of the keto-enol equilibrium constants and acid dissociation constants interrelating all keto and enol forms in that medium

The enol of α-cyano-α-phenylacetic acid was observed as a short-lived transient species formed upon flash photolytic generation of phenylcyanoketene by a photo-Wolff reaction of α-cyano-α-diazoacetophenone followed by hydration of the ketene. Rates of ketonization of the enol were measured in dilute hydrochloric acid solutions and acetic acid, biphosphate ion, tris(hydroxymethyl)methylamine, and ammonia buffers; this gave a rate profile with turning points from which the first and second acid ionization constants of the enol were determined: pK1 = 0.99 and pK2 = 8.70. Rates of enolization of the keto tautomer were also determined by bromine scavenging, and combination of these with rates of ketonization of the enol gave the keto-enol equilibrium constant pKE. = 7.22, relating the un-ionized carboxylic acid to the un-ionized enol, and the additional keto-enol equilibrium constant pK'E = 6.49, relating the carboxylate ion to the enolate monoanion. The results also provided the acidity constants pKa = 1.68 for the carboxylic acid ionizing as an oxygen acid to give the carboxylate ion, pKaK = 8.22 for the carboxylic acid ionization as a carbon acid to give the enolate monoanion, and pK'aK = 15.19 for the carboxylate ion ionizing as a carbon acid to give the enolate dianion; the latter agrees well with pK'aK = 15.25 obtained directly by monitoring the extent of carbon acid ionization of the carboxylate ion in concentrated potassium hydroxide solutions. The magnitudes of these equilibrium constants are discussed, and comparisons with other keto-enol systems are made.

Lanthanoid Complex as a Novel Carbon Dioxide Carrier for the Carboxylation of Active Methylene Compounds under Mild Conditions

A lanthanoid complex, formed by the addition of a lanthanoid alkoxide to an isocyanate, serves as a novel carbon dioxide carrier for the rapid carboxylation of active methylene compounds under mild conditions.

The Carboxylation of Active Methylene Compounds with Carbon Dioxide in the Presence of Diphenylcarbodiimide and Potassium Carbonate

Active methylene compounds were effectively carboxylated with carbon dioxide in the presence of diphenylcarbodiimide (DPC) as a biotin model and potassium carbonate.Fluorene was carboxylated even under a nitrogen atmosphere in the presence of DPC, indicating that a carbonate ion was the carbon source.The reaction occured even in the presence of water.It was considered that reaction intermediates are stable to water and that the concentration of the carbonate ion is important for carboxylation.

Synthesis of Isotopically Labelled 3-Amino-2-phenylpropionic Acid and Its Role as a Precursor in the Biosynthesis of Tenellin and Tropic Acid

A synthesis of - and -3-amino-2-phenylpropionic acids 7a and 7b is described.The incorporation of this amino acid into tenellin 1 from Beauveria bassiana (Bals.) Vuill. and into tropic acid 10 moiety of the tropane alkaloids hyscoyamine 8 and scopolamine 9 from Datura innoxia was studied but proved unsuccessful in each case.

Process for carboxylating organic substrates with carbon dioxide in hydrocarbon solvents

Carboxylable substrates i.e., ketones, esters, nitroparaffins and nitriles, containing activated hydrogen atoms are carboxylated by reaction with alkaline phenates and CO2 in at least one hydrocarbon solvent selected from aliphatic, alicyclic, aromatic and alkyl-aromatic hydrocarbon solvents.

Carboxylation of compounds

Method of carboxylating a compound of the group of R-C CH, RCH2 CN, indene, cyclopentadiene or fluorene, where R is hydrocarbyl, comprising contacting said compound with carbon dioxide under substantially anhydrous conditions in the presence of a base of the formula: SPC1 Where X is sodium or potassium, R1 is hydrogen or alkyl and subsequently acidifying the resultant reaction product to form the carboxylated product.