This is an old revision of this page, as edited by NotWith (talk | contribs) at 13:58, 10 August 2012 (Oxovitisin A). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
Revision as of 13:58, 10 August 2012 by NotWith (talk | contribs) (Oxovitisin A)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) | |
| Names | |
|---|---|
| IUPAC name Pyran-2-one | |
| Other names
α-Pyrone 2-Pyranone 2H-Pyran-2-one | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.264 
|
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| 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 , 100 kPa).
 Y 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. The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.
-
4-Pyrone
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.