2-Furanone is a
heterocyclic
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
. It is also known as γ-crotonolactone (GCL), as it is formally the
lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
Lactones are formed by intramolecular esterification of the co ...
derived from γ-hydroxy
isocrotonic acid
Isocrotonic acid (also known as quartenylic acid; formally named (''Z'')-2-butenoic acid) is the ''cis'' isomer of crotonic acid. It is an oil, possessing a smell similar to that of brown sugar. It boils at 171.9 °C, concomitant with co ...
. The chemical is colloquially called "butenolide", and is the parent structure for the
butenolide
Butenolides are a class of lactones with a four-carbon heterocyclic ring structure.Joule JA, Mills K. (2000). Heterocyclic Chemistry 4th ed. Blackwell Science Publishing: Oxford, UK They are sometimes considered oxidized derivatives of furan. The ...
class of compounds. It is a colourless liquid.
Synthesis and reactions
2-Furanone is prepared by oxidation of
furfural:
:
![Oxidation of furfural to furanone](https://upload.wikimedia.org/wikipedia/commons/6/62/Oxidation_of_furfural_to_furanone.png)
It exists in equilibrium with the
tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert.
The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hyd ...
2-hydroxy
furan, which serves as an intermediate in the interconversion between the β- and α-furanones. 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
In physiology, dehydration is a lack of total body water, with an accompanying disruption of metabolic processes. It occurs when free water loss exceeds free water intake, usually due to exercise, disease, or high environmental temperature. Mil ...
.
See also
*
:Furanones, various substituted structural analogs
*
Pyrone
Pyrones or pyranones are a class of heterocyclic 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 (or ...
, which has one more carbon atom in the ring
References
{{DEFAULTSORT:Furanone, 2-
Furanones
GHB receptor ligands