759-51-3

Usage

Chemical Properties

Yellow Oil

Uses

Intermediate in the preparation of Ethosuximide.

InChI:InChI=1/C9H13NO2/c1-4-7(3)8(6-10)9(11)12-5-2/h4-5H2,1-3H3/b8-7+

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 78-93-3 butanone 
• 125256-49-7 C₇H₁₆N₄ 
• 25468-53-5 ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate 

Downstream Products

• 24543-23-5 3-ethyl-1,2,2-tricyano-3-methyl-cyclopropanecarboxylic acid ethyl ester 
• 70289-02-0 3-Methyl-3-ethyl-2-cyan-hexansaeure-ethylester 
• 21101-83-7 2-cyano-3-methyl-3-phenyl-valeric acid ethyl ester 
• 70289-04-2 3-benzyl-2-cyano-3-methyl-valeric acid ethyl ester 
• 7309-45-7 ethyl 2-cyano-3-methylvalerate 
• 107456-80-4 2,3-Dicyan-3-methyl-2-(phenylmethyl)pentansaeure-ethylester 
• 141-82-2 malonic acid 
• 372-09-8 cyanoacetic acid 

Relevant academic research and scientific papers

Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives

In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substituted anilines has been improved using the microwave irradiation. Significantly higher yields compared to conventional condensation have been observed. The preliminary biological results indicated that some of the synthesized compounds showed promising in vitro antifungal activities towards several test fungi. 1-(4-Bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8) exhibited significant in vitro inhibitory activities against broad spectra of fungus, and on the basis of obtained data, the investigated bromo derivative has to be observed as novel potential fungicide. The density functional theory (DFT) calculations have been performed in order to study the structure-activity relationship (SAR) of the investigated molecules. In order to prediction of the chemical activity of the molecule, the molecular electrostatic potential (MEP) map was analyzed for the optimized geometry of 1-phenyl-3-ethyl-3-methylpyrrolidine-2,5-dione (4) and 1-(4-bromophenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione (8).

Novel basic ionic liquid based on alkylammonium as efficient catalyst for Knoevenagel reaction

The typical Knoevenagel condensation was carried out smoothly in the presence of a basic ionic liquid of N,N,N′,N′-tetramethyl-N′- hexyl-ethylenediammonium tetrafluoroborate ([TMHEDA]BF4), and 99% of yield was obtained using ethyl cyanoacetate and benzaldehyde as substrates at 60 °C for 1 h. Four reuses of the ionic liquid without dramatic decrease in catalytic activity for Knoevenagel condensation demonstrated the good stability and operability of the ionic liquid. Moreover, the typical nucleophilic addition reactions were also accomplished by the same ionic liquid to check its feasibility. The dual function of the basic ionic liquid both as solvent and catalyst, combined with simple product separation and recycling, is expected to contribute to the development of a green and environmentally friendly strategy. Copyright Taylor & Francis Group, LLC.

Steric effects in high pressure Knoevenagel reactions

The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes.

Synthesis of nitrogen-containing heterocycles. 7 reaction of aliphatic diaminomethylenehydrazones with hindered ethoxymethylenecyanoacetate

Aliphatic diaminomethylenehydrazones 1 were reacted with ethyl 2-cyano-3-ethoxy-2-pentenoate 2 to give a number of heterocycles in low to moderate yields, according to the substitution pattern and the size of substituent. When 1 carried a single methyl group on the terminal nitrogen, it gave preferentially 6-oxo-1,6-dihydropyrimidines 4 incorporating N(4) into the ring. In contrast, the reaction between 1c or 1d and 2 led to 6-imino- and 6-oxo-1,6-dihydropyrimidines 7 and 8 along with 3. When the alkylidene moiety was bulky, 1e and 1f, the similar reaction gave 3 in high yields without any cyclized product. Upon exposure to acid, compound 3 yielded 6-oxo-1,6-dihydropyrimidines 6, [1,2,4]triazolo[1,5-c]pyrimidine-8-carboxylate 5 and N-alkenyl-1,2,4-triazoles 9 in addition to 7 and 8 in proportions dictated by the nature of the substituents of 1. The structural assignment and reaction mechanism are discussed.

Transition metal polyhydrides-catalyzed addition of activated nitriles to aldehydes and ketones via Knoevenagel condensation

Transition metal polyhydrides and dihydrogen complexes catalyze Knoevenagel addition of cyanoacetate to aldehydes and ketones under neutral and mild conditions, the adducts undergo dehydration to give substituted (E)-2-cyano-α,β-unsaturated esters exclusively.