2-Pyrone

2-Pyrone

Chembox new
Reference= [ [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/463159 2H-Pyran-2-one] at Sigma-Aldrich]
ImageFile=2-Pyranone.pngImageSize=100px
IUPACName=Pyran-2-one
OtherNames=α-Pyrone
2-Pyranone
2"H"-Pyran-2-one
Section1= Chembox Identifiers
CASNo=504-31-4
PubChem=68154
SMILES=C1=CC(=O)OC=C1
Section2= Chembox Properties
Formula=C5H4O2
MolarMass=96.08
Appearance=
Density=1.197 g/mL
MeltingPt=
BoilingPt=102-103 °C at 20 mmHg
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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. [Woodard BT, Posner G H. "Recent Advances in Diels-Alder Cycloadditions Using 2-Pyrones." "Advances in Cycloaddition". 1999, 5, 47-83.] . The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides Fact|date=March 2008.

2-Pyrone also forms 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.

References


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  • Pyrone — Py rone, n. [G. pyron, an abbr. of pyrokoman.] (Org. Chem.) An unsaturated cyclic compound, {C5H4O2}, of which two varieties are known, [alpha] and [gamma]. [gamma] pyrone is the parent substance of several natural yellow dyestuffs …   The Collaborative International Dictionary of English

  • pyrone — [pī′rōn΄, pī rōn′] n. [Ger pyron: see PYRO & ONE] 1. either of two isomeric, unsaturated, closed chain compounds, C5H4O2, from which several yellow dyes are derived 2. any of a class of compounds derived from pyrone …   English World dictionary

  • pyrone — ● pyrone nom féminin Composé hétérocyclique C5H4O2, dérivé des pyrannes. Nom générique des dérivés de ces composés …   Encyclopédie Universelle

  • Pyrone — Pyrone,   Pyrane …   Universal-Lexikon

  • Pyrone — pyran 2 one pyran 4 one Les pyrones …   Wikipédia en Français

  • Pyrone — Pyrones or pyranones are a class of cyclic chemical compounds. They contain an unsaturated six membered ring containing one oxygen atom and a ketone functional group. There are two isomers denoted as 2 pyrone and 4 pyrone. The 2 pyrone structure… …   Wikipedia

  • pyrone — ˈpīˌrōn noun ( s) Etymology: International Scientific Vocabulary pyr + one 1. : either of two isomeric carbonyl compounds C5H4O2 derived from pyran: a. : an oily liquid delta lactone; 2H pyran 2 one calle …   Useful english dictionary

  • Pyrone — 2 Pyron 4 Pyron Pyrone oder Pyranone sind eine Gru …   Deutsch Wikipedia

  • pyrone — pironas statusas T sritis chemija formulė (O=)C₅H₄O atitikmenys: angl. pyrone rus. пирон ryšiai: sinonimas – piranonas …   Chemijos terminų aiškinamasis žodynas

  • pyrone — /puy rohn, puy rohn /, n. Chem. either of two heterocyclic ketones having the formula C5H4O2. [1890 95; PYR + ONE] * * * …   Universalium

  • pyrone — noun Any of a class of cyclic chemical compounds that contain an unsaturated six membered ring with one oxygen atom and a ketone functional group. Syn: pyranone …   Wiktionary

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