14369-81-4

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2 3-BUTADIENOATE 95 is used as a reactant for the synthesis of 9H-pyrrolo[1,2-a]indole derivatives via a phosphine-promoted Michael addition/intramolecular Wittig reaction. This application is significant in the development of new pharmaceutical compounds with potential therapeutic properties.
Used in Chemical Synthesis:
ETHYL 2 3-BUTADIENOATE 95 is used as a reactant for the synthesis of dihydropyrans by reacting with acyclic enones. This reaction is crucial in the development of new chemical compounds with various applications in different industries.
Used in Heterocyclic Chemistry:
ETHYL 2 3-BUTADIENOATE 95 is used as a reactant to synthesize spiranic heterocycles by reacting with heterocyclic bis-arylidene ketones via phosphine-catalyzed [3+2] annulations. This application is essential in the development of novel heterocycles with potential applications in various fields, including pharmaceuticals and materials science.
Used in Asymmetric Cycloaddition:
ETHYL 2 3-BUTADIENOATE 95 is used in the performance evaluation of bifunctional N-acyl aminophosphines to catalyze the asymmetric [3+2] cycloaddition of phenylidenemalononitrile. This application is vital in the development of new catalytic systems for asymmetric synthesis, which is a critical aspect of modern organic chemistry.

InChI:InChI=1/C6H8O2/c1-3-5-6(7)8-4-2/h5H,1,4H2,2H3

Upstream product

• 64-17-5 ethanol 
• 624-65-7 2-propynyl chloride 
• 64-19-7 acetic acid 
• 4341-76-8 Ethyl 2-butynoate 
• 4683-54-9 3-ethoxy-2-cyclobuten-1-one 
• 171085-78-2 Ethoxyvinylketene 
• 123-31-9 hydroquinone 
• 141-97-9 ethyl acetoacetate 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 75-36-5 acetyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 53841-07-9 ethyl cyanoacetate 

Downstream Products

• 113373-69-6 ethyl-1,2,3,5-tetrahydro-4-oxo-2-phenyl-4H-1-benzazepine-3-carboxylate 
• 796863-39-3 Methyl ethyl 2-cyclopentene-1,2-dicarboxylate 
• 212071-04-0 ethyl 1-(diphenylphosphinoyl)-2,5-dihydro-2-phenylpyrrole-3-carboxylate 
• 74-85-1 ethene 
• 50888-73-8 butadiene monoxide 
• 691-45-2 acetylketene 
• 75-07-0 acetaldehyde 
• 171085-78-2 Ethoxyvinylketene 
• 74-99-7 prop-1-yne 
• 37875-78-8 2-methyl-1,4-diphenyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 37875-81-3 2-methyl-4-phenyl-1-(4-methylphenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester 
• 37875-83-5 1-(4-chlorophenyl)-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylic acid ethyl ester 
• 84254-70-6 (1S,6R)-2-Oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl ester 
• 37875-82-4 ethyl 2-methyl-1-(4-methoxyphenyl)-4-phenyl-1,4-dihydropyridine-3-carboxylate 

Relevant academic research and scientific papers

NHC-catalyzed [4 + 2] annulations of allenoates and 2,3-dioxopyrrolidine derivatives

A facile NHC-catalyzed [2 + 4] annulation of allenoates with 2,3-dioxypyrrolidine derivatives was discovered, which paved a new avenue for the construction of highly substituted pyranopyrrole with moderate to good yields, high atom economy and mild reaction conditions. This journal is

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.

Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS2to form 2-thineyl vinyl sulfide

We have developed a DPPE-catalyzed three molecular two component tandem reaction of γ-substituted allenoate and CS2 to construct 2-thineyl vinyl sulfide through phosphine catalyzed [3+2] cyclization followed by Michael addition. The synthetic value of the

Indolizine derivative and preparation method thereof

The invention discloses an indolizine derivative and a preparation method thereof. The indolizine derivative is prepared from pyridinium bromide and allenic acid ester through [3+2] cycloaddition reaction in a reaction solvent under the action of an inorganic base catalyst and a Lewis base promoter in a nitrogen atmosphere. The reaction substrate of the preparation method is simple, easy to synthesize and low in price; wherein the [3+2] cycloaddition reaction has the advantages of mild reaction conditions, high reaction efficiency, high indolizine derivative yield and high atom economy. Therefore, the indolizine derivative has the advantages of no catalyst residue, high purity and high application value.

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

Sulfinate-Engaged Nucleophilic Addition Induced Allylic Alkylation of Allenoates

A strategically novel Pd-catalyzed nucleophilic addition induced allylic alkylation reaction (NAAA) of allenoates has been successfully accomplished. By judiciously integrating ZnCl2-promoted Michael addition with Pd-catalyzed allylic alkylation, allenoates readily undergo allyl-sunfonylation at the internal double bond, thus providing a straightforward avenue for the rapid assembly of a host of structurally diversified α-allyl-β-sufonylbut-3-enoate derivatives. The success of this transformation profits from a delicate control of the reaction kinetic of each elementary step, thanks to the synergistic interaction of Pd/Zn bimetallic system, thus suppressing either direct allylic sulfonylation or premature quenching of therein in situ generated ester enolate intermediate. Furthermore, by expanding the scope of workable Michael acceptor beyond those previously required doubly activated ones, such as methylenemalononitrile, the present work substantially enriches the repertoire of NAAA reactions.

A Scaffold-Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides

A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo-sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring-expansion method, facilitated by an increase of the ring-strain during the branching phase, led to sulfonamides bearing medium-sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors.

Stereoselective Synthesis of Functionalized Benzooxazepino[5,4- a] isoindolone Derivatives via Cesium Carbonate Catalyzed Formal [5 + 2] Annulation of 2-(2-Hydroxyphenyl)isoindoline-1,3-dione with Allenoates

In this work, we present a strategy for the stereoselective synthesis of functionalized benzooxazepino[5,4-a]isoindolone derivatives via a Cs2CO3-catalyzed domino β-addition and γ-aldol reaction of 2-(2-hydroxyphenyl)isoindoline-1,3-dione derivatives with allenoates, which offers an avenue for a combination of the structural unity between benzooxazepine and isoindolone motifs in synthetically useful yields with high stereoselectivities under mild conditions. Remarkably, it is the first example of highly stereoselective Cs2CO3-catalyzed formal [5 + 2] annulation of 2-(2-hydroxyphenyl)isoindoline-1,3-dione with allenoates.

Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols

Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.