70526-06-6

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-ethyl 3-(pyrrolidin-1-yl)but-2-enoate is utilized as a pharmaceutical intermediate for its capacity to be incorporated into the synthesis of a range of pharmaceuticals. Its unique structure allows it to contribute to the development of new medications, enhancing the therapeutic options available.
Used in Organic Synthesis:
In the realm of organic synthesis, (Z)-ethyl 3-(pyrrolidin-1-yl)but-2-enoate serves as a valuable building block. It is employed in the creation of complex organic compounds, facilitating the construction of molecules with specific functionalities and properties required for various applications in chemical research and industry.
Used in the Synthesis of Functional Materials:
Beyond its pharmaceutical applications, (Z)-ethyl 3-(pyrrolidin-1-yl)but-2-enoate is also used in the synthesis of functional materials. Its chemical structure provides a foundation for developing materials with tailored properties for use in diverse fields such as materials science, nanotechnology, and electronics.

Upstream product

• 123-75-1 pyrrolidine 
• 4341-76-8 Ethyl 2-butynoate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 158261-95-1 3-Pyrrolidino-1-butanol 
• 181058-87-7 3-diphenylhydrazono-butyric acid ethyl ester 
• 89-25-8 edaravone 
• 479077-33-3 4-ethoxycarbonyl-5-methyl-3-pyridin-4-yl-isoxazole 
• 1143-82-4 ethyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 495417-31-7 ethyl 3-(4-methoxyphenyl)-5-methylisoxazole-4-carboxylate 
• 495417-30-6 ethyl 3-(2-methoxyphenyl)-5-methylisoxazole-4-carboxylate 
• 917388-43-3 C₁₄H₁₅NO₄ 
• 108400-97-1 ethyl (4E)-2-acetyl-5-phenylpent-4-enoate 
• 400828-03-7 ethyl 2-acetyl-2-(3-phenyl-2-propenyl)-5-phenyl-4-pentenoate 
• 954230-39-8 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester 
• 1190830-84-2 ethyl 5-hydroxy-3-pyrrolidin-1-yl-6-oxo-6-phenylhex-2-enoate 
• 16880-35-6 ethyl α-(phenylimidomethyl)acetoacetate 

Relevant academic research and scientific papers

Enamines as Surrogates of Alkene Carbanions for the Reductive Alkenylation of Secondary Amides: An Approach to Allylamines

A new strategy to construct allylamines through reductive alkenylation of secondary amides with enamines is reported. The method features the use of trifluoromethanesulfonic anhydride as an activation reagent of amides, and enamines as unconventional alkenylation reagents. In this manner, enamines serve as surrogates of alkene carbanions instead of the classical enolates equivalents. A possible mechanism involving a Hoffmann-like elimination of the amine-borane complex intermediate is proposed.

Lipid accumulation inhibitory activities of novel isoxazole-based chenodeoxycholic acids: Design, synthesis and preliminary mechanism study

In continuation of our drug discovery program on hyperlipidemia, a series of novel isoxazole-chenodeoxycholic acid hybrids were designed, synthesized and evaluated for their lipid-lowering effects. Preliminary screening of all the synthesized compounds was done by using a 3T3-L1 adipocyte model, in which the most active compound 16b could significantly reduce the lipid accumulation up to 30.5% at a nontoxic concentration 10 μM. Further mechanism studies revealed that 16b blocked lipid accumulation via activating FXR-SHP signaling pathway, efficiently down-regulated the expression of key lipogenesis regulator SREBP-1c.

Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols: Selective synthesis of monoallylation products

A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.

Easily available nickel complexes as catalysts for the intermolecular hydroamination of alkenes and alkynes

A series of nickel complexes of the type [(P-P)NiX2] ((P-P) = bisphospines or bisphosphites, X = chloride, triflate) were used as catalysts for the hydroamination of both activated and unactivated alkenes and alkynes with pyrrolidine. In general, the use of activated unsaturations, such as acrylonitrile, required mild reaction conditions (e.g. 100 °C and 4 h) in comparison with other non-activated alkenes. Particularly with a series of alkynes, the use of nickel(ii) centers diminished or even inhibited the formation of otherwise undesired homocoupling and/or transfer hydrogenation by-products, such as the ones obtained in the presence of zerovalent nickel. When using less activated substrates, better selectivity was obtained, although harsher reaction conditions were needed. From a general perspective, the results of this report strongly support the potential use of nickel as a good candidate for further application in the hydroamination of organic unsaturations by means of screening of several π acceptor ligands. The Royal Society of Chemistry.

New methodologies for the synthesis of 3-acylpyridone metabolites

A core isoxazolo[4,3-c]pyridin-4-one scaffold is prepared and elaborated at C-3(Me) and C-7 as a masked building block for 3-acylpyridin-2-ones related to the acylpyridone natural products Georg Thieme Verlag Stuttgart.

Reduction of carbonyl compounds using the carbonyl reductase of kluyveromyces marxianus

A compound represented by a genera formula (Ia) or (Ib) and a stereo-selective preparation method thereof using a carbonyl reductase which is separated from Kluyveromyces marxianus. The compound can be prepared by reduction of substituted β-keto ester and can be used as an intermediate in preparing β-lactam group antibiotics.

1,3-Dipolar cycloaddition route to nitrogen heterocyclic triones

1,3-Dipolar cycloaddition of nitrile oxides, formed in situ by dehydration of primary nitro compounds, with pyrrolidine enamines of protected γ- or δ-amino-β-keto esters affords isoxazole-4-carboxylates; these undergo lactam formation and N-O bond cleavage to afford 3-acyltetramic acids and 3-acyl-4-hydroxypyridin-2-ones.

An Isoxazole Route to Unsaturated α-Alkoxycarbonyl-β-diketones

Cycloaddition of diethylphosphonomethyl nitrile oxide to the enamine from ethyl acetoacetate produces 4-ethoxycarbonyl-3-diethoxyphosphonylmethyl-5-methylisoxazole; condensation of the phosphonate with aldehydes and ketones gives 3-alkenylisoxazoles that are cleaved by hexacarbonylmolybdenum to afford unsaturated α-alkoxycarbonyl-β-diketones.

The γ-alkylation of cyclic β-ketoesters via their enamine derivatives

The γ-alkylation - functionalization of cyclic β-ketoesters via their enamine derivatives is discussed with particular emphasis on their preparation from β-ketoesters and their reaction with various electrophiles such as electrophilic olefins, halogenoids, anmd allylic and benzylic halides.Although the amine ring size does not appear to affect reactivity to a great extent, the reaction is very sensitive to β-ketoester ring size, with six-membered rings giving the best results.In the latter case the alkylation-functionalization is general and specific to the γ-position and therefore provides an important complement to the dianion and related methodologies.