2-Pyrone

2-Pyrone^[1]

Names
IUPAC name Pyran-2-one
Other names α-Pyrone 2-Pyranone 2H-Pyran-2-one
Identifiers
CAS Number	504-31-4
ChEBI	CHEBI:37965
ChemSpider	61462
Jmol interactive 3D	Image
PubChem	68154
InChI InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H Key: ZPSJGADGUYYRKE-UHFFFAOYSA-N InChI=1/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H Key: ZPSJGADGUYYRKE-UHFFFAOYAI
SMILES O=C\1O\C=C/C=C/1
Properties
Chemical formula	C5H4O2
Molar mass	96.08
Density	1.197 g/mL
Boiling point	102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes.^[2] The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.

The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element.

See also

• Pyrone

References

1. 2H-Pyran-2-one at Sigma-Aldrich
2. Woodard BT, Posner G H (1999). "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones". Advances in Cycloaddition 5: 47–83.