7686-78-4

Basic information

• Product Name: 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER
• Synonyms: 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER;diethyl 2-vinylcyclopropane-1,1-dicarboxylate;1,1-Bis(ethoxycarbonyl)-2-vinylcyclopropane;2,2-(3-Butene-1,2-diyl)malonic acid diethyl ester;2-Ethenylcyclopropane-1,1-dicarboxylic acid diethyl ester;2-Vinyl-1,1-cyclopropanedicarboxylic acid diethyl ester
• CAS NO: 7686-78-4
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24234
• EINECS: 231-695-0
• Mol File: 7686-78-4.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 230.6 °C at 760 mmHg
• Flash Point: 101.6 °C
• Appearance: /
• Density: 1.174 g/cm³
• Vapor Pressure: 0.0652mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER(7686-78-4)
• EPA Substance Registry System: 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER(7686-78-4)

Safety Data

• Hazardous Substances Data: 7686-78-4(Hazardous Substances Data)

Usage

Uses

Diethyl 2-Vinylcyclopropane-1,1-dicarboxylate used in the preparation of Vigabatri which is a novel anti-epileptic drug. Antidepressant; antipsychotic; anxiolytic.

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 1390, 1958 DOI: 10.1021/jo01103a618Tetrahedron Letters, 17, p. 2121, 1976

InChI:InChI=1/C11H16O4/c1-4-8-7-11(8,9(12)14-5-2)10(13)15-6-3/h4,8H,1,5-7H2,2-3H3

Upstream product

• 996-82-7 sodium diethylmalonate 
• 64-17-5 ethanol 
• 821-06-7 (E)-1,4-dibromobutene 
• 996-82-7 sodium diethylmalonate 
• 39198-65-7 buta-1,3-dien-t-yl-dimethyl-sulfonium; chloride 
• 105-53-3 diethyl malonate 
• 764-41-0 1,4-dichloro-2-butene 
• 1476-11-5 Z-1,4-dichlorobutene 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 6974-12-5 1,4-dibromo-2-butene 
• 5137-55-3 Aliquat 336 
• 103-83-3 N,N'-dimethylbenzylamine 
• 13654-26-7 2-Allylidene-malonic acid diethyl ester 
• 70775-39-2 dimethylsulfoxonium methylide 

Downstream Products

• 36265-86-8 1-Phenyl-5,5-diaethoxycarbonyl-pent-2-en 
• 57742-48-0 (RS)-2-Vinyl-1,1-cyclopropandicarbonsaeure 
• 86726-12-7 2-[(E)-4-(2-Hydroxy-5-methyl-phenyl)-but-2-enyl]-malonic acid diethyl ester 
• 86726-14-9 2-[(E)-4-(4-Chloro-2-hydroxy-phenyl)-but-2-enyl]-malonic acid diethyl ester 
• 86726-20-7 ethyl 6-(2-hydroxy-6-chlorophenyl)-2-carbethoxy-4-hexenoate 
• 79930-10-2 diethyl <2-(phenylethynyl)-3-butenyl>propanedioate 
• 79011-77-1 ethyl 2-oxo-5-vinyl-tetrahydrofuran-3-carboxylate 
• 92173-10-9 (4E)-ethyl 2-ethoxycarbonyl-2,4-hexadienoate 
• 7686-77-3 3-cyclopentene-1-carboxylic acid 
• 85914-66-5 diethyl (E)-5-phenylthio-3-pentene-1,1-dicarboxylate 
• 86726-11-6 2-[(E)-4-(2-Hydroxy-3-methyl-phenyl)-but-2-enyl]-malonic acid diethyl ester 
• 86726-15-0 2-[(E)-4-(2-Hydroxy-5-methoxy-phenyl)-but-2-enyl]-malonic acid diethyl ester 
• 86726-13-8 2-[(E)-4-(2-Hydroxy-3,5-dimethyl-phenyl)-but-2-enyl]-malonic acid diethyl ester 
• 82819-46-3 (E)-diethyl 2-(4-phenylbut-2-en-1-yl)malonate 

Relevant articles and documents

Copper-mediated controlled radical ring-opening polymerization (RROP) of a vinylcycloalkane

This investigation reports controlled ring-opening polymerization of a vinylcyclopropane via copper-mediated atom transfer radical polymerization which leads to predominantly 1,5 ring-opening polymerization. The Royal Society of Chemistry.

Vinyl-aziridines and cyclopropanes in Pd-catalyzed (3+2)-cycloaddition reactions with cyclic N-sulfonyl imines

Efficient palladium-catalyzed (3 + 2)-cycloaddition reactions of cyclic N-sulfonyl imines and vinyl-aziridines (or cyclopropanes) have been achieved. The reactions, with either vinylic substrate, proceed with excellent yields affording highly functionalized imidazolidine and pyrrolidine derivatives. The cycloadditions take place via the reaction of zwitterionic π-allyl palladium intermediates with cyclic N-sulfonyl imines through i) the formation of two N–C bonds in the presence of vinylaziridines (synthesis of imidazolidines) and ii) one C–C bond and one N–C bond in the presence of vinylcyclopropanes (synthesis of pyrrolidines). Following on preliminary works on the diastereoselective synthesis of imidazolidines, herein we wish to give a broader view on the subject by describing derivatization reactions and attempts towards an enantioselective version. Moreover, we describe and discuss the behavior of each vinylic substrate (aziridine or cyclopropane) on the (3 + 2)-cycloaddition reactions. Mechanistic and (intriguing) selectivity outcomes are also going to be discussed.

Palladium-Catalyzed Formal (3 + 2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes

A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.

A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin

A convenient, safe and cost-effective method for carrying out the key vinylation of 5-ethoxy-2-pyrrolidinone (8) in the preparation of 5-vinyl-2-pyrrolidinone (2) in the presence of potassium carbonate is described. This present procedure is developed by replacing inherently hazardous ethyl magnesium bromide with inexpensive and eco-friendly potassium carbonate. The reaction was performed on a multi-gram scale, with vinyl magnesium bromide as the vinylation reagent, in an 81% yield to give the 5-vinyl-2-pyrrolidinone with excellent purity and without the need for chromatography.

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.).