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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:37965 ;
ChemSpider	61462 ;
ECHA InfoCard	100.007.264
PubChem CID	68154;
CompTox Dashboard (EPA)	DTXSID50198441 ;
	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	102–103 °C at 20 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^{[citation needed]}

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.

References

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

[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.

[1]

[2]

See also

References