Undec-10-yn-1-ol

1. Long-Chain ω-Alkynol

10-Undecyn-1-ol is a long-chain terminal alkynol with the molecular formula C₁₁H₂₀O and a molecular weight of 168.28 g/mol . Its structure features a terminal carbon-carbon triple bond (C≡C) at one end and a primary hydroxyl group (-OH) at the opposite end of an eleven-carbon chain. This unique linear architecture provides two distinct reactive sites separated by a flexible methylene spacer, making it an ideal building block for constructing functionalized molecules .

2. Versatile Synthetic Intermediate and Click Chemistry Precursor

This compound serves as a valuable intermediate in organic synthesis . The terminal alkyne group readily participates in copper-catalyzed azide-alkyne cycloaddition (CuAAC), a classic "click chemistry" reaction, allowing efficient attachment to azide-functionalized molecules. It is also employed in the preparation of 11-bromo-undec-1-yne by reacting with carbon tetrabromide and triphenylphosphine, further expanding its synthetic utility . With 10 rotatable bonds and a calculated LogP of approximately 3.08 , the compound exhibits good lipophilicity and solubility in organic solvents while being immiscible with water .

3. Bioactive Compound with Antifungal Properties

10-Undecyn-1-ol exhibits significant antifungal activity, making it of interest in pharmaceutical and agrochemical research . This biological property, combined with its synthetic versatility, positions the compound as a dual-function molecule—both a bioactive agent and a synthetic precursor. It is also used in the esterification of pentanoic and stearic acids in the presence of lipase enzymes, demonstrating its utility in biocatalytic applications .