13cyclohexanedione

1,3-cyclohexanedione, also known as cyclohexane-1,3-dione, is an organic compound consisting of a six-membered ring with two ketone groups at the 1 and 3 positions. Its molecular formula is C6H8O2. It is a member of the 1,3-dicarbonyl family, a class known for enolizable protons adjacent to the carbonyls.

In solution, the molecule can tautomerize between the diketone form and enol or enolate forms under appropriate conditions. The methylene bridge between the two carbonyl groups is relatively acidic, facilitating deprotonation to form enolates that participate in a variety of carbon–carbon bond-forming reactions. This reactivity makes 1,3-cyclohexanedione a versatile building block in organic synthesis.

Applications of 1,3-cyclohexanedione center on generating substituted cyclohexane frameworks and heterocycles. Its activated 1,3-dicarbonyl motif enables condensations such as Knoevenagel and Michael-type additions with aldehydes, ketones, or activated olefins, as well as subsequent cyclizations to form novel heterocycles. Derivatives of 1,3-cyclohexanedione are used in medicinal chemistry and materials science as scaffolds for further functionalization.

Preparation methods vary and may involve oxidation or functionalization of suitable precursors; it is typically handled as a synthetic building block rather than a bulk commodity chemical. Safety considerations align with standard laboratory practices for diketones: use appropriate personal protective equipment and work in a well-ventilated area to minimize inhalation or skin exposure.