868-04-2

Usage

Uses

Used in Catalyst Evaluation:
Ethyl2-cyano-3-ethyl-2-pentenoate is used as a test compound for evaluating the effectiveness of various catalysts, particularly silica catalysts, in the Knoevenagel condensation reaction. Its synthesis can serve as a benchmark to assess the performance of different catalysts in promoting this type of condensation reaction.
Used in Organic Chemistry Research:
As a compound with unique structural features, Ethyl2-cyano-3-ethyl-2-pentenoate can be utilized in organic chemistry research for exploring novel reactions, synthesis pathways, and potential applications in the development of new chemical compounds and materials.
Used in Material Science:
The properties of Ethyl2-cyano-3-ethyl-2-pentenoate, such as its reactivity and functional groups, may make it a candidate for use in material science applications, where it could be incorporated into polymers, coatings, or other materials to impart specific characteristics or functions.

InChI:InChI=1/C10H15NO2/c1-4-8(5-2)9(7-11)10(12)13-6-3/h4-6H2,1-3H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 96-22-0 pentan-3-one 

Downstream Products

• 28456-66-8 3-Ethyl-2-cyan-pentansaeure-ethylester 
• 53608-83-6 3-ethyl-2-cyano-2-methyl-pent-3-enoic acid ethyl ester 
• 24543-21-3 3,3-Diaethyl-1,2,2-tricyan-cyclopropan-1-carbonsaeure-aethylester 
• 80721-13-7 4,4-diethyl-2,6-dioxo-piperidine-3,5-dicarbonitrile 
• 4160-95-6 3,3-diethylpentanedioic acid 
• 5692-97-7 2,2-diethylsuccinic acid 
• 6637-50-9 3,3-Diethylpentanoic Acid 

Relevant academic research and scientific papers

Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids

Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.

Carbon chain shape selectivity by the mouse olfactory receptor OR-I7

The rodent OR-I7 is an olfactory receptor exemplar activated by aliphatic aldehydes such as octanal. Normal alkanals shorter than heptanal bind OR-I7 without activating it and hence function as antagonists in vitro. We report a series of aldehydes designed to probe the structural requirements for aliphatic ligand chains too short to meet the minimum approximate 6.9 ? length requirement for receptor activation. Experiments using recombinant mouse OR-I7 expressed in heterologous cells show that in the context of short aldehyde antagonists, OR-I7 prefers binding aliphatic chains without branches, though a single methyl on carbon-3 is permitted. The receptor can accommodate a surprisingly large number of carbons (e.g. ten in adamantyl) as long as the carbons are part of a conformationally constrained ring system. A rhodopsin-based homology model of mouse OR-I7 docked with the new antagonists suggests that small alkyl branches on the alkyl chain sterically interfere with the hydrophobic residues lining the binding site, but branch carbons can be accommodated when tied back into a compact ring system like the adamantyl and bicyclo[2.2.2]octyl systems.

Ionic liquid as catalyst and reaction medium - A simple, efficient and green procedure for Knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic ionic liquid

The basic ionic liquid 1-butyl-3-methylimidazolium hydroxide, [bmIm]OH, efficiently catalyzes Knoevenagel condensation without requirement of any organic solvent. A wide range of aliphatic and aromatic aldehydes and ketones easily undergo condensations with diethyl malonate, malononitrile, ethyl cyanoacetate, malonic acid and ethyl acetoacetate. The reactions proceed at room temperature and are very fast (10-30 min). However, the most significant feature of this methodology is the condensation of aliphatic aldehyde with diethyl malonate, which is not very easy to achieve by conventional reagents, and was not addressed adequately in literature providing a general and convenient procedure. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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.

Silica-supported imines as mild, efficient base catalysts

Imine grafted silicas are found to be mild and effective base catalysts for Knoevenagel and Michael reactions.

Aminopropylated MCMs as base catalysts: A comparison with aminopropylated silica

Aminopropyl-functionalised MCMs, prepared via a one-pot method, are found to be effective base catalysts for the Knoevenagel reaction, with significant improvements in terms of turnover number and solvent dependence to the ostensibly similar aminopropylsilica.

Cycloalkylthiazoles

The invention relates to compounds of the formula: STR1 wherein R is hydrogen or lower alkyl, R1, R2, R3 and R4, independently, are hydrogen, lower alkyl, lower alkenyl, cycloalkyl or phenyl unsubstituted or substituted by up to 3 substituents independently selected from lower alkyl, lower alkoxy or halogen, or R1 and R2 taken together with the carbon atom are alkylene of 2 to 5 carbon atoms unsubstituted or substituted by lower alkyl, and n is an integer of from 0 to 3, and, when R1 is different from R2 and/or when R3 is different from R4, enantiomers, diastereomers and racemates thereof and, when R is hydrogen, salts thereof with pharmaceutically acceptable bases. The compounds of formula I and, when R is hydrogen, pharmaceutically exceptable salts thereof are useful as bronchopulmonary agents, for example, in the relief of asthma and allergic reactions.

CINETIQUE ET MECANISME DE LA REACTION DE KNOEVENAGEL DANS LE BENZENE-2 REACTION DU MALONITRILE ET DE LA (+) METHYL-3 CYCLOHEXANONE EN PRESENCE D'UNE AMINE PRIMARIE PURE ET DE SON MELANGE AVEC L'ACIDE ACETIQUE

The kinetics of the reaction of (+)-3-methyl cyclohexanone with malonitrile were studied in benzene at 25 deg C, in the presence of hexylamine-acetic acid mixtures.Hexylamine gives an imine with cyclohexanone in an acid-catalyzed step.This imine then reacts quickly with malononitrile.A rate law of zero order in malononitrile is observed.Separate kinetic results obtained for the formation of the imine and for the imine-malonitrile reaction support this mechanism.Without acetic acid, a complex rate law is observed; hexylamine acts mainly as a basic catalyst.Primary amine-carboxylic acid was used as a catalyst in Knoevenagel reaction, often giving an increase in yield and a diminution in the reaction time compared with the more commonly used catalysts: piperidine, β-alanine, AcOH-AcONH4.

Geminate-Substituted Cyclopentadienes. 1. Synthesis of 5,5-Dialkylcyclopentadienes via 4,4-Dialkylcyclopent-2-en-1-ones.

A synthetic route for the preparation of 5,5,-dialkylcyclopentadienes (1) via 4,4-dialkylcyclopent-2-en-1-ones (3) is described.Beginnig with ketones (in which the two carbonyl substituents will become the two alkyl groups in the title compounds), the route traverses the Guareschi imides 5, 3,3-dialkylglutaric acids 4 and their ethyl esters 7, masked acyloins 8, cyclopentenones 3, alkohols 9, and bromides 10 to reach the dienes 1.Physical properties of five such derivates 1 and 3 (dimethyl, methylethyl,diethyl, methyl-n-propyl, and methylisopropyl) are presented.