2-Pyrone: Difference between revisions
Updating {{chembox}} (changes to verified fields - added verified revid - updated 'CASNo_Ref', 'Verifiedfields', 'Watchedfields', 'verifiedrevid') per Chem/Drugbox validation (report errors or [... |
Temperatures (melting, boiling, autoignite, flash) use convert tempalte to calculate. using AWB |
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| verifiedrevid = 477215588 |
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|Reference=<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/463159 2H-Pyran-2-one] at [[Sigma-Aldrich]]</ref> |
| Reference =<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/463159 2H-Pyran-2-one] at [[Sigma-Aldrich]]</ref> |
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|ImageFile=2-Pyranone.png |
| ImageFile =2-Pyranone.png |
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|ImageSize=100px |
| ImageSize =100px |
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|IUPACName=Pyran-2-one |
| IUPACName =Pyran-2-one |
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|OtherNames=α-Pyrone<br>2-Pyranone<br>2''H''-Pyran-2-one |
| OtherNames =α-Pyrone<br>2-Pyranone<br>2''H''-Pyran-2-one |
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|Section1= |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 61462 |
| ChemSpiderID = 61462 |
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| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N |
| StdInChIKey = ZPSJGADGUYYRKE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo=504-31-4 |
| CASNo =504-31-4 |
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| PubChem =68154 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 37965 |
| ChEBI = 37965 |
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| SMILES = O=C\1O\C=C/C=C/1 |
| SMILES = O=C\1O\C=C/C=C/1 |
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|Section2= |
|Section2={{Chembox Properties |
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| Formula =C<sub>5</sub>H<sub>4</sub>O<sub>2</sub> |
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| MolarMass =96.08 |
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| Appearance = |
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| Density =1.197 g/mL |
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| MeltingPt = |
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| BoilingPtC = 102 to 103 |
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| BoilingPt=102–103 °C at 20 mmHg |
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| Boiling_notes = at 20 mmHg |
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| Solubility= |
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| Solubility = |
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| MainHazards= |
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| FlashPt= |
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| Autoignition= |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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Revision as of 01:10, 28 November 2014
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| Names | |
|---|---|
| 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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| ChEBI | |
| 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 to 103 °C (216 to 217 °F; 375 to 376 K) |
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]
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.