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Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-cyano-3-methylcrotonate is used as a reactant for the preparation of pyrones and pyridines, which are important heterocyclic compounds with potential applications in the development of pharmaceutical agents. The cyclization of ylidenemalononitrile and ylidenecyanoacetate enamines, facilitated by Methyl 2-cyano-3-methylcrotonate, allows for the synthesis of these valuable heterocyclic structures.
Used in Chemical Synthesis:
In the field of chemical synthesis, Methyl 2-cyano-3-methylcrotonate is utilized as a versatile building block for the creation of a wide range of organic compounds. Its unique structure allows it to participate in various types of reactions, such as cyclization, addition, and substitution, making it a valuable asset in the synthesis of complex organic molecules.
Used in Research and Development:
Methyl 2-cyano-3-methylcrotonate is also employed in research and development settings, where it is used to explore new reaction pathways and investigate the properties of novel chemical compounds. Its reactivity and structural features make it an interesting subject for study, contributing to the advancement of knowledge in organic chemistry and related fields.

InChI:InChI=1/C7H9NO2/c1-5(2)6(4-8)7(9)10-3/h1-3H3

Upstream product

• 372-09-8 cyanoacetic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 105-34-0 methyl 2-cyanoacetate 
• 107-95-9 3-amino propanoic acid 
• 67-64-1 acetone 
• 186581-53-3 diazomethane 
• 53982-98-2 2-cyano-but-2-enoic acid methyl ester 
• 759-72-8 2-cyano-crotonic acid 
• 60-29-7 diethyl ether 

Downstream Products

• 524-01-6 isorenieratene 
• 73435-80-0 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenenal 
• 4651-98-3 2-amino-4-methylthiophene-3-carboxylic acid methyl ester 
• 96914-63-5 trans-1-cyano-2,2-dimethyl-1-(methoxycarbonyl)-3-phenylcyclopropane 
• 96914-62-4 cis-1-cyano-2,2-dimethyl-1-(methoxycarbonyl)-3-phenylcyclopropane 
• 14533-86-9 methyl (E)-2-cyano-3-phenylprop-2-enoate 

Relevant academic research and scientific papers

Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.

Synthesis and Reactivity Profile of Ylidenemalononitrile Enamines and Their Ester Analogs Towards Electrophiles and Nucleophiles

Herein, we describe the synthesis and reactivity of enamines derived from ylidenemalononitriles and ylidenecyanoacetates. The enamine scope was expanded by (1) increasing yields of aldehyde-derived ylidenemalononitriles, (2) incorporating silyl functional

Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

Inactivation of the NF-κB signaling pathway by inhibition of IKKβ is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKβ inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-α, which are well-known inflammatory responses generated by activated NF-κB. However, no inhibitory activity against IKKβ was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 μM. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML.

NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A

The present invention relates to novel carboxamide compounds, pharmaceutical compositions containing them, and their use in therapy. The compounds possess valuable therapeutic properties and are particularly suitable for treating or controlling medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders

A substrate-driven approach to determine reactivities of α,β-unsaturated carboxylic esters towards asymmetric bioreduction

The degree of C=C bond activation in the asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases was studied, and general recommendations to render these "borderline-substrates" more reactive towards enzymatic reduction are proposed. The concept of "supported substrate activation" was developed. In general, an additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates, and α-cyano groups showed little effect. The alcohol moiety of the ester functionality was found to have a strong influence on the reaction rate. Overall, activities were determined by both steric and electronic effects. Biotransformation: The asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases could be tuned by varying the degree of C=C bond activation (see scheme). An additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates. Copyright

New syntheses of retinal and its acyclic analog γ-retinal by an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation. A formal route to lycopene and β-carotene

Since the C15 β-end-group aldehyde 10 ((β-ionylidene) acetaldehyde), an excellent intermediate in the syntheses of retinoids, can be synthesized in many ways from β-ionone, and since the corresponding acyclic C15 ψ-end-group aldehyde 5 can easily be synthesized from citral (1) (Scheme 3), we applied the C15 + C5 route to the syntheses of γ-retinal ((all-E)-8) (Scheme 3) and retinal ((all-E)-13) (Scheme 4), and therefore, by coupling (2 x C20 → C 40), to the preparation of lycopene (14) and β-carotene (15) (Scheme 5). Our new syntheses of retinal ((all-E)-13) and γ-retinal ((all-E)-8 use an extended aldol reaction with a C6 building block that incorporates a C5 unit after decarboxylation.

A new biomimetic-like aromatization of the cyclic end groups of terpenoids with stereospecific migration of one of the methyl groups: A convenient route to isorenieratene (φ,φ-carotene)

The synthesis of isorenieratene, a natural carotenoid isolated from the marine sponge Reniera japonica and from some anoxygenic phototrophic bacteria or nonphotosynthetic actinomycetes, was performed from α-, β- and retro-ionones. In this series of cycloh

A convenient and selective one-pot method for the synthesis of monosubstituted secondary alkyl malononitriles

We have found that α,α-dicyanoalkenes can be efficiently and selectively reduced to α,α-dicyanoalkanes (malononitriles) with NaBH4 in 95% EtOH at 0 °C. In addition, we have determined that the condensation of malononitrile with ketones using absorption alumina as a catalyst can be followed directly, in one pot, by reduction with NaBH 4 in 95% EtOH at 0 °C to provide the monosubstituted secondary alkyl malononitriles in good to excellent yields (42-94%). This procedure provides a convenient alternative to direct alkylation of malononitrile or reduction of α,α-dicyanoalkene intermediates.

Cycloalkyl carboxylic acid amides, their production and their use as fungicides in agriculture

The present invention relates to cycloalkylcarboxamides of formula I where: A is optionally substituted C3-C6-cycloalkyl; Alk is straight-chain or branched C1-C6-alkylene; R1is optionally substituted C1-C6-alkyl or C2-C6-alkenyl; R2, R3is hydrogen, or is optionally halogenated C1-C6-alkyl or C2-C6-alkenyl; W is an optionally substituted fused bicyclic ring system having in each case six ring atoms, where one or two carbon ring atoms may be replaced by nitrogen atoms; and their agriculturally useful salts. Furthermore, the invention relates to fungicidal compositions comprising a compound of formula I as crop protection agent.

KNOEVENAGEL CONDENSATION CATALYSED BY ALUMINIUM OXIDE.

The Knoevenagel condensation of carbonyl compounds with active methylene compounds was readily carried out with aluminium oxide as catalyst.