112825-92-0

Basic information

• Product Name: Propanedioic acid, [5-(methoxycarbonyl)-2-cyclohexen-1-yl]-, diethyl ester, cis-
• CAS NO: 112825-92-0
• Molecular Formula: C15H22O6
• Molecular Weight: 298.336
• Mol File: 112825-92-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [5-(methoxycarbonyl)-2-cyclohexen-1-yl]-, diethyl ester, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [5-(methoxycarbonyl)-2-cyclohexen-1-yl]-, diethyl ester, cis-(112825-92-0)
• EPA Substance Registry System: Propanedioic acid, [5-(methoxycarbonyl)-2-cyclohexen-1-yl]-, diethyl ester, cis-(112825-92-0)

Safety Data

• Hazardous Substances Data: 112825-92-0(Hazardous Substances Data)

Upstream product

• 54911-89-6 cis-methyl 5-hydroxycyclohex-3-enecarboxylate 
• 34727-00-9 lithium diethyl malonate 
• 121232-18-6 methyl cis-<5-(diphenylphosphino)acetoxy-3-cyclohexene-1-carboxylate> 
• 144681-44-7 methyl cis-<5-oxy-3-cyclohexene-1-carboxylate> 
• 144681-43-6 methyl cis-<5-oxy-3-cyclohexene-1-carboxylate> 
• 144681-42-5 methyl cis-<5-(N-benzylcarbamoyl)oxy-3-cyclohexene-1-carboxylate> 
• 144681-45-8 methyl cis-<5-(N-phenylthiocarbamoyl)oxy-3-cyclohexene-1-carboxylate> 
• 144681-41-4 methyl cis-<5-(ethoxycarbonyl)oxy-3-cyclohexene-1-carboxylate> 
• 60729-55-7 cis-methyl 5-acetoxycyclohex-3-enecarboxylate 
• 87802-98-0 cis-5-[(methoxycarbonyl)oxy]-3-cyclohexene-1-carboxylic acid methyl ester 
• 105-53-3 diethyl malonate 

Relevant articles and documents

Highly selective allylic alkylation with a carbon nucleophile at the more substituted allylic terminus catalyzed by an iridium complex: An efficient method for constructing quaternary carbon centers

The selective construction of quaternary carbon centers, which are frequently found in natural products, is essential to many syntheses. A new method relying on the iridium complex [Ir(cod)Cl]2 as the catalyst can be used for the allylic alkylation of acyclic compounds 1. The products are obtained in yields between 70 and 85% and with a selectivity of 100%, cod = cyclooctadiene.

Stereochemistry of the palladium-catalyzed allylic substitution: The synanti dichotomy in the formation of (π-allyl)palladium complexes and their equilibration

The mechanism of palladium(0)-catalyzed allylic substitution has been investigated with the aim of finding whether or not the intermediate (π-alryl)palladium complexes can arise in a syn fashion as an alternative to the well known anti-mechanism. Using (diphenylphosphino)acetate as a leaving group and stereochemically biased substrates 30b and 35b evidence for the syn stereochemistry has been acquired (30b → 31 and 35b → 36). This reversal of stereochemistry is facilitated by severe steric congestion in the starting allylic esters (which impairs the ordinary anti-mechanism) and is boosted by the pre-coordination of the Pd(0) reagent to the leaving group. The latter effect apparently lowers the activation entropy. With cyclohexene derivatives 10b, 18b, and 19b and acyclic substrate 25b, where steric hindrance does not operate, the anti-mechanism producing η3-complexes dominates even for (diphenylphosphino)acetates. At elevated temperature, rapid equilibration of η3-complexes (13 ? 14 and 20 ? 21) has been observed prior to the reaction with a nucleophile. This effect has been attributed to the presence of (diphenylphosphino)acetate ion acting as a ligand for palladium.