134149-18-1

Basic information

• Product Name: 1,1-Cyclopentanedicarboxylic acid, 2-methylene-, dimethyl ester
• CAS NO: 134149-18-1
• Molecular Formula: C10H14O4
• Molecular Weight: 198.219
• Mol File: 134149-18-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,1-Cyclopentanedicarboxylic acid, 2-methylene-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Cyclopentanedicarboxylic acid, 2-methylene-, dimethyl ester(134149-18-1)
• EPA Substance Registry System: 1,1-Cyclopentanedicarboxylic acid, 2-methylene-, dimethyl ester(134149-18-1)

Safety Data

• Hazardous Substances Data: 134149-18-1(Hazardous Substances Data)

Upstream product

• 932-88-7 1-iodo-2-phenylethyne 
• 130905-55-4 dimethyl 4-pentenylmalonate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 93185-10-5 dimethyl 2-(pent-4'-enyl)malonate 

Relevant articles and documents

Ligand, Solvent, and Deuterium Isotope Effects in Mn(III)-Based Oxidative Free-Radical Cyclizations

Oxidation of β-keto ester 1 with Mn(pic)3 and Cu(OAc)2 affords bicycloalkane 8, not the expected alkene 7, which is formed in high yield with Mn(OAc)3 and Cu(OAc)2.A series of control experiments established that the most likely explanation for this observation is that Mn(pic)2, but not Mn(OAc)2, reacts with the bicyclic radical 5 more rapidly than Cu(OAc)2 does.These studies also indicate the potential for improved yields from oxidative free-radical cyclization of deuterated substrates.For instance, reaction of β-keto ester 1-d with 2 equiv of Mn(OAc)3 and no Cu(OAc)2 affords 65percent of 8, whereas β-keto ester 1 provides only 22percent of 8 under the same conditions.Large kinetic isotope effects change the nature of the termination step and prevent the formation of acyclic radical 3 by intermolecular hydrogen transfer.Solvent and ligand effects on the oxidation of β-keto ester 1, malonate 14, and acetylenic β-keto ester 25 are described.

SYNTHESIS OF ETHYNYLIDENE CYCLOPENTANES BY A CYCLISATION CATALYZED BY THE SIMULTANEOUS PRESENCE OF PALLADIUM (0) AND COPPER (I)

Ethynylidene cyclopentanes 3 can be formed in 35-71percent yield from the reaction of the enolates of compounds such as δ-acetylenic malonates with 1-halogeno-1-alkynes.This reaction requires catalysis by both palladium (0) and copper (I) species.

Solvent Effects on Manganese(III)-Based Oxidative Free-Radical Cyclizations: Ethanol and Acetic Acid

Ethanol complements the typical solvent, acetic acid, for Mn(III)-based oxidative free-radical cyclizations.Cyclization of enol ether 1c to give gibberellic acid intermediate 6c is successfull in ethanol, but not in acetic acid.Ethanol acts as a reducing