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
Names
IUPAC name
1,2-oxazole
Other names
isoxazole
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.472
Properties
C3H3NO
Molar mass 69.06202 g/mol
Density 1.075 g/ml
Boiling point 95 °C (203 °F; 368 K)
Acidity (pKa) -3.0 (of conjugate acid) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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) and a neurotransmitter agonist AMPA. 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]