Chemistry:Butynone
Butynone is an organic compound and the simplest ynone. It is a reagent used in organic synthesis as a dienophile and Michael acceptor.
Preparation
The triisopropylsilyl derivative of butynone is prepared by oxidation of the corresponding derivative of 2-butynol, itself prepared from TIPS acetylene by deprotonation followed by nucleophilic addition to acetaldehyde.[1]
Applications
Butynone was one of the reagents used in the discovery of the Bohlmann–Rahtz pyridine synthesis.[2]
Butynone and its derivatives participate in cycloaddition reactions, yielding a variety of heterocycles. The electron-deficient alkyne group participates in the azide-alkyne Huisgen cycloaddition to produce 1,2,3-triazine methyl ketones.[3] [4+2+1] cycloaddition with 1,2-phenylenediamine and furfural derivatives gives benzodiazepine rings.[4]
Sources
- ↑ James A. Marshall, Patrick Eidam, and Hilary Schenck Eidam (2008). "Synthesis of 4-triisopropylsilyl-3-butyn-2-ol by asymmetric transfer hydrogenation". Organic Syntheses 84: 120. http://www.orgsyn.org/demo.aspx?prep=v84p0120.
- ↑ Bagley, Mark; Glover, Christian; Merritt, Eleanor (2007). "The Bohlmann-Rahtz Pyridine Synthesis: From Discovery to Applications". Synlett (16): 2459–2482. doi:10.1055/s-2007-986674.
- ↑ Bakka, Thomas A.; Strøm, Morten B.; Andersen, Jeanette H.; Gautun, Odd R. (2017). "Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation". Bioorganic & Medicinal Chemistry 25 (20): 5380–5395. doi:10.1016/j.bmc.2017.07.060. PMID 28797773.
- ↑ Jiang, Jingjing; Queneau, Yves; Popowycz, Florence (2023). "Ammonium Acetate Catalyzed Formation of 1,5-Benzodiazepines through [4+2+1] Cycloaddition Involving 5-Hydroxymethylfurfural". European Journal of Organic Chemistry 26 (19). doi:10.1002/ejoc.202300144.
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