In organic chemistry, an ynone is an α,β-unsaturated ketone with the structure R1C≡C‒C(=O)R2 (R2 ≠ H) in which the carbonyl (C=O) function is conjugated to a C≡C triple bond at the α,β position. Capillin is an example of a naturally occurring ynone.
- Diynone: an ynone with two triple bonds on both sides[clarification needed] of the carbonyl group.
- Bis-ynone: a structure with two ynone groups in it. These can undergo an intramolecular cycloaddition to form furan derivatives.
One method for synthesizing ynones is the acyl substitution reaction of an alkynyldimethylaluminum with an acyl chloride. An alkynyldimethylaluminum compound is the reaction product of trimethylaluminum and a terminal alkyne.
An alternative but longer synthetic method involves the reaction of an alkynyllithium compound with an aldehyde. The reaction produces a secondary alcohol that then can be oxidized via the Swern oxidation.
- "CHEBI:51723 - ynone". ChEBI. ebi.ac.uk. Retrieved 18 May 2017.
- Wills, M.S.B.; Danheiser, R.L. (August 28, 1998). "Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Ynones. Formation of Polycyclic Furans via the Generation and Rearrangement of Strained Heterocyclic Allenes". J. Am. Chem. Soc. 120 (36): 9378–9379. doi:10.1021/ja9819209.
- Wang, Baomin; Bonin, Martine; Micouin, Laurent (June 22, 2005). "A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides". J. Org. Chem. 70 (15): 6126–6128. doi:10.1021/jo050760y. PMID 16018717.
- Weijiang, Sun; Wang, Yan; Wua, Xuan; Yao, Xiaoquan (2013). "Palladium-, ligand-, and solvent-free synthesis of ynones by the coupling of acyl chlorides and terminal alkynes in the presence of a reusable copper nanoparticle catalyst". Green Chemistry. 15 (9): 2356–2360. Retrieved 18 May 2017.
- Wang, Zhaofeng; Li, Li; Yong, Huang (August 18, 2014). "A General Synthesis of Ynones from Aldehydes via Oxidative C–C bond Cleavage under Aerobic Conditions". J. Am. Chem. Soc. 136 (35): 12233–12236. doi:10.1021/ja506352b. PMID 25133731.
- Media related to Ynones at Wikimedia Commons