65726-93-4

Basic information

• Product Name: Cyclohexanecarboxylic acid, 2-oxo-1-(2-propenyl)-, 2-propenyl ester
• CAS NO: 65726-93-4
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• Mol File: 65726-93-4.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 2-oxo-1-(2-propenyl)-, 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 2-oxo-1-(2-propenyl)-, 2-propenyl ester(65726-93-4)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 2-oxo-1-(2-propenyl)-, 2-propenyl ester(65726-93-4)

Safety Data

• Hazardous Substances Data: 65726-93-4(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 18709-01-8 2-hydroxycyclohex-1-enecarboxylic acid 
• 108-94-1 cyclohexanone 
• 372-09-8 cyanoacetic acid 
• 15022-08-9 diallylcarbonate 
• 5453-93-0 allyl 2-oxocyclohexane-1-carboxylate 

Downstream Products

• 94-66-6 2-allylcyclohexan-1-one 
• 5277-36-1 2,2-diallylcyclohexanone 

Relevant articles and documents

A NEW ONE-POT METHOD FOR α,α-DIALLYLATION OF KETONES BASED ON THE PALLADIUM-CATALYZED REACTION OF ALLYLIC CARBONATES AND ALLYL β-KETO CARBOXYLATES UNDER NEUTRAL CONDITIONS

A new method for α,α-diallylation of ketones catalyzed by palladium-phosphine complexes under neutral conditions has been developed.Allylation of β-keto carboxylates with allylic carbonates, followed by the decarboxylation-allylation as a one-pot reaction affords diallylated ketones in good yields.

Specific Two-Step Decarboxylation of Copper(I,II) β-Keto Carboxylates. A Novel Type of Regulation of the Decarboxylation of β-Keto Acids

Copper(I,II) β-keto carboxylates undergo a specific two-step decarboxylation.For example, the decarboxylation of copper(I) 1-oxocyclohexane-2-carboxylate (1) evolves CO2 in a 50percent yield in dimethylformamide (DMF) at 70 deg C.No further CO2 evolution beyond this 50percent decarboxylation occurs at 70 deg C.At a higher temperature of 120 deg C., the remaining 50percent of the CO2 is released.This specific two-step decarboxylation of 1 results from the intermediate formation of a dicopper(I) salt of the enol of 1-oxocyclohexane-2-carboxylic acid (10) which is stable to decarboxylation at 70 deg C.Compound 10 is isolated from the reaction mixture after the 50percent decarboxylation.Decarboxylations of copper(I,II) benzoylacetates, copper(I) oxaloacetate, copper(II) 1-oxo-cyclohexane-2-carboxylate, and copper(II) chloride 1-oxocyclohexane-2-carboxylate also proceed stepwise in DMF.On the other hand, copper(I,II) benzoylcyclopropane-1-carboxylates without an enolizable α-hydrogen atom evolve CO2 in a usual one-step manner.The present specific two-step decarboxylation of copper(I,II) β-keto carboxylates provides a novel type of regulation of the decarboxylation of β-keto acids and also a method of generating copper(I,II) enolate.The bearing of the two-step decarboxylation of copper(I) β-keto carboxylates on both the Cu(I)-mediated carboxylation of ketones and organic synthesis is also described.