17447-60-8

Usage

Uses

Used in Organic Synthesis:
2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of reactions, making it a valuable building block for the creation of complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is used as a starting material for the development of new drugs. Its versatile chemical properties enable the synthesis of a variety of drug candidates with potential therapeutic applications.
Used in Chemical Research:
2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its unique structure provides researchers with valuable insights into the behavior of similar compounds and the development of novel synthetic strategies.
Used in Material Science:
In the field of material science, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester can be used as a monomer for the production of polymers with specific properties. Its incorporation into polymer structures can lead to materials with enhanced mechanical, thermal, or electrical characteristics, depending on the desired application.
Overall, 2-Vinylcyclopropane-1,1-dicarboxylic acid dimethyl ester is a versatile and valuable compound with a wide range of applications across various industries, including organic synthesis, pharmaceuticals, chemical research, and material science. Its unique structure and reactivity make it an essential component in the development of new products and technologies.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3825, 1985 DOI: 10.1016/S0040-4039(00)89261-8

Upstream product

• 102060-82-2 (E)-dimethyl 2-(4-((methoxycarbonyl)oxy)but-2-en-1-yl)malonate 
• 292638-85-8 acrylic acid methyl ester 
• 1476-11-5 Z-1,4-dichlorobutene 
• 108-59-8 malonic acid dimethyl ester 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 821-06-7 (E)-1,4-dibromobutene 
• 5332-81-0 carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester 
• 122471-25-4 {CH₂CHCHCH₂CH(COOCH₃)2}Co(CO)3 
• 4111-54-0 lithium diisopropyl amide 
• 6974-12-5 1,4-dibromo-2-butene 
• 145838-86-4 bis(methoxycarbonyl)(phenyliodinio)methanide 
• 106-99-0 buta-1,3-diene 
• 166302-22-3 2-(Carboxy-trimethylsilanyl-methyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 51534-74-8 dimethyl 3-oxopropane-1,1-dicarboxylate 

Downstream Products

• 100520-02-3 1-butoxy-2-phenylsulfanyl-ethane 
• 128065-32-7 dimethyl 3-butoxy-4-vinylcyclopentane-1,1-dicarboxylate 
• 128065-21-4 1,1-dimethoxycarbonyl-3-p-toluenesulfonylmethyl-4-vinylcyclopentane 
• 128065-22-5 1,1-dimethoxycarbonyl-3-methyl-3-p-toluenesulfonyl-4-vinylcyclopentane 
• 112723-44-1 N-phenyl-2,2-bis(methoxycarbonyl)-4-vinylbutyrolactam 
• 914785-34-5 dimethyl 5-(dimethylphenylsilyl)-3-pentene-1,1-dicarboxylate 
• 115821-64-2 dimethyl 5-(triphenylstannyl)-3-pentene-1,1-dicarboxylate 

Relevant academic research and scientific papers

Indium(III) Chloride-Promoted Intramolecular Addition of Allylstannanes to Alkynes

In the presence of an equimolar amount of InCl3, 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl3 gave 2-all

Bifunctional Organo/Metal Cooperatively Catalyzed [3 + 2] Annulation of para-Quinone Methides with Vinylcyclopropanes: Approach to Spiro[4.5]deca-6,9-diene-8-ones

A novel [3 + 2] annulation between para-quinone methides and vinylcyclopropanes for the synthesis of spiro[4.5]deca-6,9-diene-8-ones has been described. The palladium and phosphine-thiourea cooperative catalysis system played an important role in high yields and diastereoselectivities. The reaction exhibited good functional group tolerance and scalability.

Palladium-catalyzed diastereo- And enantioselective [3 + 2] cycloaddition of vinylcyclopropanes with azadienes: Efficient access to chiral spirocycles

Benzofuran-derived azadienes (BDAs) have been widely used as four-atom synthons in transition-metal-mediated cycloaddition reactions, while the exploitation of their reactivity as a two-atom unit to construct spirocycles is still underdeveloped. Herein, we reported the first palladium(0)-catalyzed diastereo- and enantioselective [3 + 2] annulation of vinylcyclopropanes (VCPs) and BDAs. This transformation is featured with a broad substrate scope (31 examples), allowing for facile access to a variety of enantioenriched spirocycles bearing a quaternary stereogenic center in good yields with excellent regio-, diastereo-, and enantioselectivities (up to 93% yield, >20:1 dr, and mostly >99% ee) under mild reaction conditions. Moreover, the spirocyclic products could be efficiently converted to structurally complex tricyclo[8.3.0.01,5]-azatridecane and tricyclo[7.3.0.01,5]-azadodecane skeletons.

Diastereoselective synthesis of tetrahydrofurans via palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes

(Chemical Equation Presented) Palladium(0)-catalyzed cycloadditions of malonate-derived vinylcyclopropane 1 and aldehydes to afford 2,5-cis disubstituted tetrahydrofuran derivatives are described. Pd loadings as low as 0.5 mol % were effective in catalyzing the transformation with high yields and diastereoselectivities. Electron-poor aldehydes work best, suggesting that a mechanism involving an initial aldol reaction may be operative.

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

(3+2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiocyanate: A Facile and Efficient Synthesis of 2-Amino-4,5-dihydrothiophenes

An easy and efficient route to obtain 2-amino-4,5-dihydrothiophenes is presented. A formal (3+2)-cycloaddition of donor-acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf) 3delivers the desired products in good to excellent yields. A broad range of functional groups is tolerated during this process.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

Pd-Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction

Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane–anthranil complex which has been confirmed by NMR experiments.

Photoredox catalysed allylic trifluoromethylation via ring opening of vinyl cyclopropanes using Langlois reagent

Trifluoromethylation of vinylcyclopropanes (VCPs) has been developed under mild reaction conditions to synthesize allylic trifluoromethylated derivatives with high yield and E/Z selectivity using visible light photo-redox catalysis and Langlois reagent (CF3SO2Na) as a trifluoromethylation source. Further, we demonstrate a gram scale synthesis procedure for a trifluoromethylation of vinylcyclopropane.

Palladium-Catalyzed Allylic Alkylation of Aldimine Esters with Vinyl-Cyclopropanes to Yield α,α-Disubstituted α-Amino Acid Derivatives

A synthetically useful approach for the synthesis of functionalized α, α-disubstituted α-amino acid derivatives via palladium-catalyzed 1,7 addition of readily available aldimine esters to vinylcyclopropanes is reported. This methodology was operated under mild conditions, affording α-allylic α-amino esters in good to excellent yields and excellent regio- and stereoselectivity. This transformation displays broad functional-group tolerance and enantioselective allylic alkylation has also been realized using a chiral phosphine ligand to provide the desired product. (Figure presented.).