cyclononan2ol

Cyclononan-2-ol is a cyclic alcohol with the chemical formula C9H18O. It belongs to the class of organic compounds known as cycloalkanes, characterized by a ring structure with a hydroxyl (–OH) functional group attached to the second carbon atom of a nine-membered carbon ring. This compound is a colorless liquid at room temperature and is notable for its relatively flexible nine-membered ring, which can adopt various conformations due to reduced ring strain compared to smaller cycloalkanes.

The synthesis of cyclononan-2-ol typically involves the reduction of cyclononan-2-one, a cyclic ketone, using reducing agents such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4). Alternatively, it can be prepared through the hydroboration-oxidation of cyclononan-2-ene or via ring-closing metathesis (RCM) followed by selective reduction. Its structure allows for potential applications in organic synthesis, particularly as an intermediate in the preparation of more complex cyclic compounds.

Cyclononan-2-ol exhibits moderate polarity due to the presence of the hydroxyl group, influencing its solubility in polar solvents like water and alcohols. It is relatively stable under normal conditions but can undergo oxidation to form cyclononan-2-one or participate in esterification reactions with carboxylic acids. Due to its unique ring size, it serves as a model compound for studying the conformational behavior of medium-sized cycloalkanes.

In research, cyclononan-2-ol has been explored in the context of supramolecular chemistry and as a building block for macrocyclic structures. Its properties make it useful in studying the effects of ring size on molecular flexibility and reactivity. While not widely commercialized, it remains a subject of interest in academic and industrial organic synthesis.