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词条 2-Furanone
释义

  1. Synthesis and reactions

  2. See also

  3. References

{{chembox
| Watchedfields = changed
| verifiedrevid = 477213431
| ImageFileL1 = Furan-2-one.svg
| ImageSizeL1 = 120
| ImageAltL1 = Skeletal formula of 2-furanone
| ImageFileR1 = 2-Furanone-3D-balls.png
| ImageSizeR1 = 130
| ImageAltR1 = Ball-and-stick model of the 2-furanone molecule
| IUPACName = 5H-furan-2-one
| OtherNames = furan-2-one, γ-crotonolactone, butenolide
| Section1 = {{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C17601
| InChI = 1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
| InChIKey = VIHAEDVKXSOUAT-UHFFFAOYAD
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 166223
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VIHAEDVKXSOUAT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 497-23-4
| PubChem = 10341
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 38118
| SMILES = O=C\\1OC/C=C/1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9917
| MeSHName = butenolide
| Section2 = {{Chembox Properties
| Formula = C4H4O2
| MolarMass = 84.07336
| Appearance =
| Density = 1.185 g/cm3, liquid
| MeltingPtC = 4 to 5
| MeltingPt_ref=[1]
| BoilingPtC = 86 to 87
| BoilingPt_notes= 12 mm Hg[1]
| Solubility =
| Section7 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

2-Furanone is a heterocyclic organic compound. It is also known as γ-crotonolactone (GCL), as it is formally the lactone derived from γ-hydroxyisocrotonic acid. The chemical is colloquially called "butenolide", and is the parent structure for the butenolide class of compounds. It is a colourless liquid.

Synthesis and reactions

2-Furanone is prepared by oxidation of furfural:[2]

It exists in equilibrium with the tautomer 2-hydroxyfuran, which serves as an intermediate in the interconversion between the β- and α-furanones.{{explain|reason=What are the alpha and beta forms?|date=October 2017}} The β form is the more stable. The interconversion is catalyzed by base.

2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration.

See also

  • Category:Furanones, various substituted structural analogs
  • Pyrone, which has one more carbon atom in the ring

References

1. ^Sigma-Aldrich Chemicals Product detail
2. ^{{cite journal|last1=Näsman|first1=Jan H.|title=3-Methyl-2(5H)-furanone|journal=Organic Syntheses|date=1990|volume=68|page=162|doi=10.15227/orgsyn.068.0162}}
{{GHBergics}}{{DEFAULTSORT:Furanone, 2-}}

2 : Furanones|GHB receptor ligands

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