2-Pyrone: Difference between revisions
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'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an [[unsaturated]] cyclic chemical compound with the [[molecule|molecular]] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. |
'''2-Pyrone''' ('''α-pyrone''' or '''pyran-2-one''') is an [[unsaturated]] cyclic chemical compound with the [[molecule|molecular]] formula C<sub>5</sub>H<sub>4</sub>O<sub>2</sub>. It is [[isomer]]ic with [[4-pyrone]]. |
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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 reaction]]s to form bicyclic [[lactone]]s. For example, it readily undergoes [[Diels-Alder reaction]]s with [[alkyne]]s producing, upon loss of [[carbon dioxide]], substituted [[benzene]]s.<ref>Woodard BT, Posner G H. "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones." ''Advances in Cycloaddition''. 1999, 5, 47-83.</ref>. The '''Gogte Synthesis''' (1938) is a method for the alkylation of certain pyrones with acid chlorides {{Fact|date=March 2008}}. |
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 reaction]]s to form bicyclic [[lactone]]s. For example, it readily undergoes [[Diels-Alder reaction]]s with [[alkyne]]s producing, upon loss of [[carbon dioxide]], substituted [[benzene]]s.<ref>Woodard BT, Posner G H. "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones." ''Advances in Cycloaddition''. 1999, 5, 47-83.</ref>. The '''Gogte Synthesis''' (1938) is a method for the alkylation of certain pyrones with acid chlorides {{Fact|date=March 2008}}. |
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Image:4-Pyranone.png|4-Pyrone |
Image:4-Pyranone.png|4-Pyrone |
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The most famous natural products are [[Bufanolides]] and [[Kavalactones]] or [[Kavapyrones]]. |
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==References== |
==References== |
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Revision as of 15:36, 1 April 2010
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| Names | |
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| IUPAC name
Pyran-2-one
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| Other names
α-Pyrone
2-Pyranone 2H-Pyran-2-one | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.264 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| 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).
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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].
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4-Pyrone
The most famous natural products are Bufanolides and Kavalactones or Kavapyrones.
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.