2-Furanone

Chembox new
ImageFile = Furan-2-one.png ImageSize = 100px
IUPACName = 5H-furan-2-one
OtherNames =
Section1 = Chembox Identifiers
CASNo = 497-23-4
PubChem = 10341
SMILES = C1C=CC(=O)O1
ChemSpiderID = 9917
MeSHName = butenolide
Section2 = Chembox Properties
Formula = C₄H₄O₂
MolarMass = 84.07336
Appearance =
Density = 1.185 g/cm³, liquid
MeltingPt = 4-5°CSigma-Aldrich Chemicals [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/283754 Product detail] ]
BoilingPt = 86-87°C (@ 12 mm Hg)
Solubility =
Section7 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

2-Furanone, also furan-2-one, is a heterocyclic chemical compound classified as a lactone. It is a common component of natural products synthesized by biochemical pathways in organisms, especially plants of the genus "Angelica". 2-Furanone is also known as "γ-crotonolactone" or "β-angelica lactone". It is the simplest butenolide compound and is colloquially called "butenolide" in the context of natural product synthesis.

Tautomerism

The tautomer of 2-furanone is known as 2-hydroxyfuran. It is unstable and rarely detected in solution, but serves as a reactive intermediate in the interconversion between the β and α lactones. The β form is the more stable but interconversion can be catalyzed by the addition of base.

Reactions

2-Furanones can be converted to furans by a two-step process of reduction followed by dehydration. First the carbon-oxygen double bond is reduced by the attachment of a trimethylsilyl functional group to the oxygen atom. The dehydration reaction introduces two carbon-carbon double bonds in the ring.

References