2-Pyrone: Difference between revisions
Devon Fyson (talk | contribs) m add See Also pyrone |
Devon Fyson (talk | contribs) removed image of 4-pyrone: no context, it has it's own page, and can compare them on pyrone page. |
||
| Line 42: | Line 42: | ||
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>{{cite journal | author = Woodard BT, [[Gary H. Posner|Posner G H]] | title = Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones | journal = Advances in Cycloaddition | year = 1999 | volume = 5 | pages = 47–83}}</ref> The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.{{Citation needed|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>{{cite journal | author = Woodard BT, [[Gary H. Posner|Posner G H]] | title = Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones | journal = Advances in Cycloaddition | year = 1999 | volume = 5 | pages = 47–83}}</ref> The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.{{Citation needed|date=March 2008}} |
||
<gallery> |
|||
Image:4-Pyranone.png|4-Pyrone |
|||
</gallery> |
|||
The most common natural products containing a 2-pyrone are the [[bufanolide]]s and [[kavalactone]]s. [[Oxovitisin A]], a pyranoanthocyanin found in wine, also contains a 2-pyrone element. |
The most common natural products containing a 2-pyrone are the [[bufanolide]]s and [[kavalactone]]s. [[Oxovitisin A]], a pyranoanthocyanin found in wine, also contains a 2-pyrone element. |
||
Revision as of 02:07, 21 February 2014
| |
| Names | |
|---|---|
| IUPAC name
Pyran-2-one
| |
| Other names
α-Pyrone
2-Pyranone 2H-Pyran-2-one | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.264 |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
| |
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.
See also
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.