63965-89-9

Basic information

• Product Name: Propanedioic acid, (2-oxocyclohexyl)-, dimethyl ester
• CAS NO: 63965-89-9
• Molecular Formula: C11H16O5
• Molecular Weight: 228.245
• Mol File: 63965-89-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, (2-oxocyclohexyl)-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, (2-oxocyclohexyl)-, dimethyl ester(63965-89-9)
• EPA Substance Registry System: Propanedioic acid, (2-oxocyclohexyl)-, dimethyl ester(63965-89-9)

Safety Data

• Hazardous Substances Data: 63965-89-9(Hazardous Substances Data)

Upstream product

• 910612-69-0 (2-morpholin-4-yl-cyclohex-1-enyl)-malonic acid dimethyl ester 
• 4922-47-8 1-(phenylthio)cyclohex-1-ene 
• 108-59-8 malonic acid dimethyl ester 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 145838-86-4 bis(methoxycarbonyl)(phenyliodinio)methanide 
• 868-26-8 dimethyl 2-bromomalonate 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 6773-29-1 dimethyl diazomalonate 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 108-94-1 cyclohexanone 
• 37457-08-2 cyclohexane-1,1-diylbis(phenylsulfane) 
• 17851-97-7 1-tri(n-butyl)stannyloxy-1-cyclohexene 
• 63965-81-1 2-(2-Methoxy-cyclohex-2-enyl)-malonic acid dimethyl ester 
• 71911-61-0 6-bicyclo<3.1.0>hexan-6-ol 

Downstream Products

• 90535-24-3 (2-oxo-cyclohexyl)-malonic acid 
• 1438-96-6 (2-oxocyclohexyl)acetic acid 

Relevant articles and documents

Electrophilic Activation of Iodonium Ylides by Halogen-Bond-Donor Catalysis for Cross-Enolate Coupling

The umpolung alkylation of silyl enol ethers with an iodonium(III) ylide proceeds under mild conditions to afford various 1,4-dicarbonyl compounds in high yields in the presence of a halogen-bonding catalyst. Unlike typical transition-metal activation processes of such ylide precursors, which tend to proceed via carbenoid intermediates, experimental and computational studies indicate that halogen bonding (XB) between the XB donor catalyst and the iodonium ylide plays a crucial role in promoting the reaction. The identification of a compatible Bronsted base catalyst enabled the extension of this method to enols generated in situ to give the corresponding adducts in good yields.

Synthetic utility of stannyl enolates as radical alkylating agents

(Equation presented) The radical-initiated β-ketoalkylation of haloalkanes with tributylstannyl enolates is described. Stannyl enolates derived from aromatic ketones are reactive toward the homolytic β-ketoalkylation of simple haloalkanes as well as those activated by an electron-withdrawing group. The reactivity of stannyl enolates as radical alkylating agents can be utilized for an efficient three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.

Malonate Anion Induced Favorskii-Type Rearrangement. Reaction of Cyclic α-Halo Ketones with Sodiomalonates

The reaction of 2-chlorocyclohexanone (1b) with ethyl sodiomalonate in benzene at 0-25 deg C gave 6-bicyclohexan-6-ol (4c), the Favorskii-type intermediate, in 49percent yield, in place of the substitution product ethyl C-(2-oxocyclohexyl)malonate (3).Derivatives of bicycloheptan-7-ol (4a,b) and those of bicyclohexan-6-ol (4d,e) were also obtained in good yields by similar means.Compound 4c was transformed into 3 readily by heating with 0.05 equiv of NaH in benzene.The hydrolysis of 4a-d with 0.2 N NaOH followed by pyrolysis at 110-120 deg C gave the ring-contracted β-keto esters 9a-d.Pyrolysis after the hydrolysis with 2N NaOH gave the corresponding ketones 11a-d in good yields.Oxidation of 4c with CrO3 and HClO4 afforded ethyl C-(2-hydroxycyclopentanecarbonyl)malonate (14) in 45 percent yield.Treatment of 4c with Br2 gave ethyl C-(1-bromocyclopentanecarbonyl)malonate (18) in 64 percent yield.