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. The ...

. 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 con ...

. 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 Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs ...

: :

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 hydr ...

2-hydroxy

furan Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly ...

, 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

s 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 ...

References

{{DEFAULTSORT:Furanone, 2- Furanones GHB receptor ligands

Synthesis and reactions

See also

References