Isoxazole

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Isoxazole
Full structural formula Skeletal formula with numbers
Ball-and-stick model Space-filling model
Identifiers
CAS number 288-14-2
PubChem 9254
ChemSpider 8897 YesY
ChEBI CHEBI:35595 YesY
ChEMBL CHEMBL13257 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H3NO
Molar mass 69.06202
Density 1.075 g/ml
Boiling point 95 °C
Acidity (pKa) -3.0 (of conjugate acid) [1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Isoxazole is an azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the univalent radical derived from isoxazole.

Isoxazole rings are found in some natural products, such as ibotenic acid. Isoxazoles also form the basis for a number of drugs, including the COX-2 inhibitor valdecoxib (Bextra). A derivative, furoxan, is a nitric oxide donor.

An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin.

The synthetic androgenic steroid danazol also has an isoxazole ring.

See also[edit]

References[edit]

  1. ^ Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).

External links[edit]