61788-30-5

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 2-cyano-2-cyclopentylacetate is used as a versatile intermediate in the synthesis of various pharmaceuticals due to its reactivity and ability to facilitate molecular transformations. Its cyano group contributes to its acidic properties, making it a valuable component in the development of new drugs.
Used in Agrochemical Synthesis:
In the agrochemical industry, Ethyl 2-cyano-2-cyclopentylacetate serves as a key building block for the synthesis of various agrochemicals, including pesticides and herbicides. Its unique chemical properties allow for the creation of effective and targeted agrochemicals.
Used in Organic Chemistry Research:
Ethyl 2-cyano-2-cyclopentylacetate is utilized as a valuable intermediate in organic chemistry research, enabling the exploration of new reactions and the development of innovative synthetic pathways.
Used in Drug Discovery and Development:
Due to its potential biological activities, such as anti-inflammatory properties and as a potential cholinesterase inhibitor, Ethyl 2-cyano-2-cyclopentylacetate is used in drug discovery and development. Its presence in various chemical structures allows researchers to investigate its therapeutic potential and incorporate it into novel drug candidates.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Ethyl 2-cyano-2-cyclopentylacetate is employed as a key component in the design and synthesis of new pharmaceutical agents. Its unique properties and reactivity make it an essential tool for the development of innovative and effective medications.

InChI:InChI=1/C10H15NO2/c1-2-13-10(12)9(7-11)8-5-3-4-6-8/h8-9H,2-6H2,1H3

Upstream product

• 5407-83-0 ethyl 2-cyano-2-cyclopentylideneacetate 
• 5732-87-6 2-cyclopentylacetonitrile 
• 105-58-8 Diethyl carbonate 
• 105-56-6 ethyl 2-cyanoacetate 
• 142-29-0 cyclopentene 
• 120-92-3 cyclopentanone 
• 60-29-7 diethyl ether 
• 137-43-9 Cyclopentyl bromide 

Downstream Products

• 5660-81-1 2-cyclopentylpropanedioic acid 

Relevant academic research and scientific papers

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.

Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon-Carbon Bond Formation Driven by the Rhodium-Catalyzed Water-Gas Shift Reaction

The rhodium-catalyzed water-gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2-3 mol %), carbon monoxide (10 bar), water (2-50 equiv), and triethylamine (2.5-7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including aliphatic and aromatic aldehydes, as well as cyclic ketones, in moderate to high yields. This method is comparable to, and for certain aspects, surpasses the established reductive alkylation protocols.

Development of drug intermediates by using direct organocatalytic multi-component reactions

Development of drug intermediates by using direct amino acid organocatalytic multi-component reaction was investigated. Hydrogenations of double-bond containing compounds including carbonyls, imines and olefins are important for living organisms as well as for the industrial production of chemicals. Amino acid catalysis has emerged as a powerful green synthetic tool for the development of both achiral and chiral catalysis of condensations and cycloadditions and the 1,2- and 1,4-additions of enals, enones and ketones including electrophiles. It was found that the amino acid proline 4a catalyzes the Knoevenagel condenstion of cyclohexanone 1a with the CH-acid ethyl cyanoacetate 2a to furnish the active olefin 9aa. This simple and environmentally friendly approach can be used to construct highly substituted hydrogenated products in a regioselective fashion with good yields.

A remarkable effect of bases on the catalytic radical addition of cyanoacetates to alkenes using a Mn(II)/Co(II)/O2 redox system

A remarkable addition effect of bases, like AcOK, was observed in the radical addition of cyanoacetates to alkenes catalyzed by a Mn(II)/Co(II)/O 2 redox system. Thus, a carbon radical from ethyl cyanoacetate could be catalytically generated by

CARBON-CARBON BOND FORMATION USING MANGANESE(III) ACETATE AS AN ELECTROCHEMICAL MEDIATOR

Anodic oxidation in a solution containing a variety of olefins and a small amount of Mn(OAc)2*4H2O brought about Mn+3-mediated carbon-carbon bond formation, such as efficient carboxymethylation of styrene derivatives to the corresponding γ-aryl-γ-butyrolactones, and selective coupling of active methylene compounds with non-activated monoolefins, unconjugated dienes or 5-arylpent-1-enes.

Selective Coupling of Non-Activated Olefins with Ethyl Cyanoacetate by Mn(3+)-Mediated Anodic Oxidation

Novel carbon-carbon bond formation of non-activated olefins with ethyl cyanoacetate has been developed by anodic oxidation using only small amount of Mn(OAc)2*4H2O to give selectively either saturated or unsaturated coupling products depending upon the pr

REACTIVITY OF CYCLOALKENES IN THE RADICAL ADDITION REACTION WITH ETHYL CYANOACETATE

The effect of ring size on the reactivity of C5 to C12 cycloalkenes in the copper(II) oxide catalysed and dibenzoyl peroxide initiated addition reaction with ethyl cyanoacetate was determined at 90 deg C using the method of competition reactions. cis-Cycl