2-Pyrone
From Wikipedia, the free encyclopedia
| 2-Pyrone[1] | |
|---|---|
 |
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| IUPAC name | Pyran-2-one |
| Other names | α-Pyrone 2-Pyranone 2H-Pyran-2-one |
| Identifiers | |
| CAS number | [504-31-4] |
| PubChem | |
| SMILES | C1=CC(=O)OC=C1 |
| Properties | |
| Molecular formula | C5H4O2 |
| Molar mass | 96.08 |
| Density | 1.197 g/mL |
| Boiling point |
102-103 °C at 20 mmHg |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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].
2-Pyrone also forms the the core structure of a variety of natural organic compounds. For example, the coumarins are an important class of compounds which are benzo-fused derivatives of 2-pyrone.
 4-Pyrone |
 Coumarin |
[edit] References
- ^ 2H-Pyran-2-one at Sigma-Aldrich
- ^ Woodard BT, Posner G H. "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones." Advances in Cycloaddition. 1999, 5, 47-83.
