1619-58-5

Usage

Chemical Properties

colorless liquid

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 576, 1942 DOI: 10.1021/ja01255a033

InChI:InChI=1/C7H11NO2/c1-3-6(5-8)7(9)10-4-2/h6H,3-4H2,1-2H3

Upstream product

• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 75-03-6 ethyl iodide 
• 109-74-0 propyl cyanide 
• 105-58-8 Diethyl carbonate 
• 143-33-9 sodium cyanide 
• 533-68-6 2-bromobutyric acid ethyl ester 
• 74-96-4 ethyl bromide 
• 105-56-6 ethyl 2-cyanoacetate 
• 64-17-5 ethanol 
• 65221-11-6 ethyl (E)-2-cyanobut-2-enoate 
• 151-50-8 potassium cyanide 
• 592-04-1 mercury(II) cyanide 
• 686-33-9 ethyl 2-cyanobut-2-enoate 
• 75-07-0 acetaldehyde 

Downstream Products

• 152995-07-8 (ethyl-phenyl-hydrazono)-cyano-acetic acid ethyl ester 
• 100453-11-0 2-ethyl-2-cyano-3-methyl-hexanoic acid ethyl ester 
• 98432-42-9 6-amino-5-ethyl-1-methylpyrimidine-2,4(1H,3H)-dione 
• 59062-33-8 2-(4-bromo-phenylazo)-2-cyano-butyric acid ethyl ester 
• 42412-18-0 3-phenylhydrazono-butyronitrile 
• 100056-03-9 2-ethyl-2-cyano-succinic acid diethyl ester 
• 76646-63-4 2-cyano-N-phenylbutanamide 
• 857771-13-2 2-ethyl-2-cyano-5-oxo-3-phenyl-hexanoic acid ethyl ester 
• 73747-27-0 2-cyanobutyramide 
• 67171-03-3 Ethyl-(2'-cylohexenyl)-cyanessigsaeureethylester 
• 14122-31-7 2-Ethoxycarbonimidoyl-2-fluoro-butyric acid ethyl ester 
• 53481-05-3 2-ethylpentanedioc acid dimethyl ester 
• 5593-71-5 <3-Aethoxycarbonyl-3-cyan-2-methyl-pent-1-enyl>-phosphonsaeure-diaethylester 
• 34741-24-7 (±)-ethyl 2-(aminomethyl)butanoate 

Relevant academic research and scientific papers

Quinazolinone Compound and Application Thereof

The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

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.

Thiazole formation through a modified Gewald reaction

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.

Efficient preparation of α,α-dialkyl-α-(phenylselanyl) acetates and α,β-unsaturated esters from the corresponding α,α-dialkyl-α-cyanoacetates by a lithium naphthalenide induced reductive selenenylation process

An array of α,α-dialkyl-α-(phenylselanyl)acetates has been synthesized very efficiently from readily available α,α- dialkyl-α-cyanoacetates, by use of lithium naphthalenide induced reductive α-selenenylation as a key operation. Moreover, the selanyl esters thus generated in situ could be converted further, in a one-pot treatment with hydrogen peroxide and acetic acid, into the corresponding α,β- unsaturated esters in moderate to high yields. The C=C bond formation was highly regio- and/or diastereoselective in some cases. Georg Thieme Verlag Stuttgart.

Synthesis of variously 9,9-dialkylated octahydropyrimido [3,4-a]-s-triazines with potential antifungal activity

9,9-Dialkyloctahydropyrimido[3,4-a]-s-triazines were synthesized by iminodimethylation reaction between a 5,5-dialkyl-6-aminopyrimidine-2,4(3H,5H)-dione, a substituted aniline and two moles of formaldehyde. The synthesis of 5,5-dialkyl-6-aminopyrimidinedione consisted of the condensation of urea with ethyl 2,2-dialkylcyanoacetates. 18 Octahydropyrimido[3,4-a]-s-triazines were synthesized and compounds resulting from a supplementary aminomethylation were also obtained. Most of these compounds were tested for antifungal activity in vitro. Only 9,9-dibutyl-6,8-dioxo-3(2-chlorophenyl)2,3,4,5,6,7,8,9-octahydropyrimido[3, 4-a]-s-triazine showed some activity against Microsporum canis.

Enzymatic alkylation of α-cyanoketones by bakers yeast

In an organic solvent system, 3-oxo-3-arylpropanenitriles are C- alkylated by bakers yeast. The reported mechanism for bakers yeast alkylation of ethyl cyanoacetate (13), in an aqueous system, has been revised.

Chemo-enzymatic alkylation of active methylene compounds

Active methylene compounds undergo chemical condensation in water with aldehydes derived from yeast oxidation of the corresponding alcohols. Unsaturated compounds so obtained are then further reduced by yeast.

Process for preparing esters of cyanoacetic acids

A novel process for preparing an ester of cyanoacetic acid which comprises reacting a cyanoacetaldehyde acetal, hydroxylamine and an alcohol.

Reactivity of the Perhalogenoalkanes CF2BrX (X = Cl, Br) with Nucleophiles. Part 4. Condensation with Carbanions

The condensation of CF2BrX (X = Cl, Br) with different carbanions is described.CF2BrX reacts with lithium acetylides and with substituted, active methylene compounds.The limits of reactivity of this reagent as well as the mechanism involved in the condens