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4-Pyrone

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4-Pyrone
Names
Preferred IUPAC name 4H-Pyran-4-one
Other names γ-Pyrone
4-Pyranone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.305 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4O2/c6-5-1-3-7-4-2-5/h1-4HKey: CVQUWLDCFXOXEN-UHFFFAOYSA-N
  • InChI=1/C5H4O2/c6-5-1-3-7-4-2-5/h1-4HKey: CVQUWLDCFXOXEN-UHFFFAOYAG
SMILES
  • C1=COC=CC1=O
  • O=C\1/C=C\O/C=C/1
Properties
Chemical formula C5H4O2
Molar mass 96.08
Melting point 32 to 34 °C (90 to 93 °F; 305 to 307 K)
Boiling point 210 to 215 °C (410 to 419 °F; 483 to 488 K)
Hazards
Flash point 101 °C (214 °F; 374 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4-Pyrone (γ-pyrone or pyran-4-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2.It is isomeric with 2-pyrone.

Preparation

4-Pyrone is prepared via the thermal decarboxylation of chelidonic acid.

Reactions

4-Pyrone and its derivatives react with amines in protic solvents to form 4-Pyridones.

Derivatives

4-Pyrone forms the central core of several natural chemical compounds, including maltol, meconic acid, kojic acid, and of the important class of the Flavones.

Maltol Kojic acid

See also

References

  1. 4H-Pyran-4-one at Sigma-Aldrich
  2. ^ Weygand, Conrad (1972). Hilgetag, G.; Martini, A. (eds.). Weygand/Hilgetag Preparative Organic Chemistry (4th ed.). New York: John Wiley & Sons, Inc. pp. 533–534, & 1009. ISBN 0471937495.
  3. Van Allan, J. A.; Reynolds, G. A.; Alessi, J. T.; Chie Chang, S.; C. Joines, R. (1971). "Reactions of 4-pyrones with primary amines. A new class of ionic associates". Journal of Heterocyclic Chemistry. 8 (6): 919–922. doi:10.1002/jhet.5570080606.
  4. Cook, Denys (1963). "The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones". Canadian Journal of Chemistry. 41 (6): 1435–1440. doi:10.1139/v63-195.
  5. Wilk, Wolfram; Waldmann, Herbert; Kaiser, Markus (2009). "Γ-Pyrone natural products—A privileged compound class provided by nature". Bioorganic & Medicinal Chemistry. 17 (6): 2304–2309. doi:10.1016/j.bmc.2008.11.001. PMID 19042133.
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