7251-97-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Cyano-pentanedioic acid diethyl ester is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving the efficacy of existing ones.
Used in Agrochemical Industry:
2-Cyano-pentanedioic acid diethyl ester is also utilized as an intermediate in the production of agrochemicals, playing a role in the development of pesticides and other agricultural chemicals to enhance crop protection and yield.
Used in Medicinal Chemistry:
2-Cyano-pentanedioic acid diethyl ester serves as a building block in the preparation of various derivatives, which have potential applications in medicinal chemistry for the discovery and design of novel therapeutic agents.
Used in Materials Science:
In the field of materials science, 2-Cyano-pentanedioic acid diethyl ester is used to create new materials with specific properties, such as improved strength, flexibility, or chemical resistance, for various industrial applications.
Safety Note:

InChI:InChI=1/C10H15NO4/c1-3-14-9(12)6-5-8(7-11)10(13)15-4-2/h8H,3-6H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 623-72-3 ethyl 3-hydroxypropanoate 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 140-88-5 ethyl acrylate 
• 105-56-6 ethyl 2-cyanoacetate 
• 7677-24-9 trimethylsilyl cyanide 
• 105-36-2 ethyl bromoacetate 
• 539-74-2 Ethyl 3-bromopropionate 
• 292638-85-8 acrylic acid methyl ester 
• 97-64-3 ethyl 2-hydroxypropionate 

Downstream Products

• 10444-38-9 ethyl 4-cyanobutyrate 
• 84763-56-4 Diethyl-1-cyan-1-(3-oxocyclohexyl)-1,3-propandicarboxylat 
• 926030-94-6 C₁₈H₂₂N₂O₅ 

Relevant academic research and scientific papers

Cu-Catalyzed cyanoalkylation of electron-deficient alkenes with unactivated alkyl bromides

We here report the photoinduced Cu-catalyzed cyanoalkylation of electron-deficient alkenes by using alkyl bromides as alkylation reagents. In the reactions, 1°, 2°, and 3° unactivated alkyl bromides with various sensitive functional groups were well tolerated with good yields. Notably, terminal and internal alkenes, as well as alkene-containing peptides, were all tolerated well.

Diastereoselective Synthesis of and Mechanistic Understanding for the Formation of 2-Piperidinones from Imines and Cyano-Substituted Anhydrides

2-Piperidinones are synthesized in a single step from imines and 2-cyano glutaric anhydrides. The reaction provides the products in good diastereoselectivity and generates a quaternary stereogenic center. Substitutions on the anhydride skeleton are well tolerated to provide 2-piperidinones with three stereogenic centers from a single transformation. The pertinent transition structures have also been computed using quantum mechanics and reveal the key interactions controlling the stereochemical outcome of the reaction.

Base-catalysed intramolecular hydroamination of vinyl sulfiies

Small amounts of n-butyllithium catalyse the highly efficient hydroamination of a large variety of vinyl sulfides. This novel methodology offers an easy access to a wide range of nitrogen heterocycles, including simple pyrrolidines and piperidines, as well as more complex bicyclic compounds. Subsequent transformations of the sulfur group led to the formation of functionalised alkaloid-like substructures. Wiley-VCH Verlag GmbH & Co. KGaA.

Nickel complexes of nio-functionalized n-Heterocyclic carbenes as precatalysts for michael reactions in air at room temperature under the much preferred base-Free conditions

A series of several new nickel precatalysts supported over N/O-functionalized N-heterocyclic carbenes (NHC) for the Michael reactions of B-dicarbonyl, B-keto ester, B-diester, and a-cyano ester compounds with a,B-unsaturated carbonyl compounds in air at ambient temperature under the much preferred base-free conditions are reported. Specifically, the nickel complexes, [1-(R1-aminocarbonylmethyl)-3-R2-imid-azol-2-ylidene]2Ni [R1 =2-C6H4(OMe); R2 = Me (1b), iPr (2b), CH2Ph (3b) and R1 = 2-CH2C4H3O; R2 =Me (4b), CH2Ph (5b)] carried out the highly convenient base-free Michael addition of the activated C-H compounds across a,B-unsaturated car- bonyl compounds in air at room temperature. The complexes 1b-5b were synthesized by the direct reaction of the respective imidazolium chloride salt with NiCl2-6H2Oin CH3CN in the presence of K2CO3 as a base. The exceptional stability of 1b-5b has been attributed to the deeply buried nickel-NHC CT-bonding molecular orbitals as evidenced from the density functional theory (DFT) studies. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Use of condensed pyrimidine derivatives for the treatment of autoimmune and inflammatory diseases

The invention relates to the use of a compound of the formula I, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for use in modulating an immune or inflammatory response: wherein: Z = O or S; n = 1-3; R3 = -CO2R8, -C(O)SR8, -C(O)NHR8, -C(S)OR8, -C(S)SR8, -C(S)NHR8, -C(NH)SR8 or -C(NH)NHR8, wherein R8 is -H or alkyl; R4 = -H, -CH2R5 or -CH2CH2R5, wherein R5 independently has one of the meanings of R3; B = -NR2-, -CH2NR2-, -CH2CH2NR2-, -CH2CHR7- or -CH2O-, wherein R2 is H or a C1-3 alkyl, alkenyl or alkynyl group, and R7 is H or a C1-3 alkyl or alkoxy group; A = wherein R1 = -NH2 or -OH, C and D are each, independently, a 5- or 6-membered, substituted or unsubstituted, aromatic or non-aromatic ring which may also contain one or more heteroatoms, and C is connected to group B in any available position.

Binary caesium-lanthanum oxide supported on MCM-41: A new stable heterogeneous basic catalyst

Heterogeneous mesoporous stable basic catalysts have been prepared by wet or solid-state impregnation of MCM-41 with caesium acetate and lanthanum nitrate followed by thermal decomposition. 133Cs MAS NMR data of CsLa/MCM-41 show an increase in

SYNTHESIS OF POLYFUNCTIONAL ALIPHATIC CARBONYL COMPOUNDS UNDER PHASE-TRANSFER CONDITIONS

We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and β-halopropionic acids and addition of the CH acids mentioned and their analogues to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products.We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the synthesis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

One-Pot Synthesis of cis Fixed β-Diketones of Bicycloalkanes, 2

Starting from 2-cycloalken-1-ones 1 the substituted cis fixed β-diketones of bicycloalkanes 4 have been obtained by a combined Michael addition of α,α,ω-alkanetricarboxylates (and related species) 2 and Dieckmann cyclization of the intermediates 3.Reactions of the β-diketone system as well as modifications of the disubstituted malonate system of 4 are reported.