32774-63-3

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 41732-05-2 2-(phenylaminomethylidene)cyclohexane-1,3-dione 
• 77959-69-4 N-[(2,6-dioxocyclohexylidene)methyl]urea 

Downstream Products

• 57440-71-8 1-(5-Methoxy-3-oxopentyl)-1-methyl-1.3-cyclohexandion 
• 57440-68-3 2-methyl-2-(3-oxopentyl)-1,3-cyclohexanedione 
• 35155-66-9 3-chloro-2-methoxycyclohex-2-en-1-one 
• 53696-38-1 2-(1-Methyl-2,6-dioxo-cyclohexylmethyl)-acrylic acid ethyl ester 
• 6971-52-4 3-methoxy-2-methylphenol 
• 25112-91-8 3-methoxy-2-methylcyclohex-2-en-1-one 
• 128813-43-4 3-(1-methyl-3-phenylselenopropanoxy)-2-methylcyclohex-2-en-1-one 
• 85335-98-4 4-(phenylthio)-6-methylbicyclo<4.4.0>deca-1,3-dien-7-one 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 128813-44-5 3-(but-3-ynyloxy)-2-methylcyclohex-2-en-1-one 
• 56671-83-1 3-bromo-2-methylcyclohex-2-en-1-one 
• 150765-78-9 2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate 
• 19424-29-4 4,4,5,5-tetramethyl-1,3-dioxolan-2-one 
• 20643-20-3 3-ethoxy-2-methyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit

Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si- to the carbonyl. The pentamethyldisilanyl group has advantages over other silicon units that are used in Tamao-Fleming procedures.

Solvent Effects on Keto-Enol Equilibria: Tests of Quantitative Models

The effect of solvent on the equilibrium constants between selected keto-enol isomer pairs has been determined.The protomeric systems studied are 5,5-dimethyl-1,3-cyclohexanedione (1), 2-methyl-1,3-cyclohexanedione (3), 3-oxabicyclo-2,9-dioxononane (5), 2,4-pentanedione (7), ethyl 3-oxobutanoate (9), and 9-anthracenone (11).A wide variety of theoretical and empirical solvation parameters have been tested in a multiparameter linear free energy format to model the changes in equilibria.The most successful correlations are obtained with the Kamlet-Taft polarity-polarizability and hydrogen-bonding terms, although the Swain A and B factors have advantages in same cases.In general, for the isomer pairs in which the enol cannot form an internal hydrogen bond (1-2, 3-4, and 11-12), the equilibria appear to be controlled almost completely by the hydrogen-bonding basicity of the solvent.For the isomer pairs 5-6, 7-8, and 9-10, in which intramolecular hydrogen bonding is possible, the polarity-polarizability effect dominates, although differential stabilization of the isomers by hydrogen bonding remains significant.

A Method for the C-Methylation of Cyclic β-Dicarbonyl Compounds

Cyclic β-dicarbonyl compounds (1, 4, 7, 10) were reacted with either aniline or urea in the presence of trimethoxymethane to give the enamines 2, 5, 8 and 11, resp.The latter were reduced with hydrogen over palladium-charcoal or with the dimethylamine-bor