Isoxazole
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| Names | |||
|---|---|---|---|
| IUPAC name
1,2-oxazole | |||
| Other names
isoxazole | |||
| Identifiers | |||
288-14-2  | |||
| 3D model (Jmol) | Interactive image | ||
| ChEBI | CHEBI:35595 | ||
| ChEMBL | ChEMBL13257 | ||
| ChemSpider | 8897 | ||
| ECHA InfoCard | 100.005.472 | ||
| PubChem | 9254 | ||
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| 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). | |||
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| 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
- Oxazole, an analog with the nitrogen atom in position 3.
- Pyrrole, an analog without the oxygen atom.
- Furan, an analog without the nitrogen atom.
- Simple aromatic rings
References
- ↑ Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).
External links
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