Oksazol

Oksazol
IUPAC ime
Identifikacija
CAS registarski broj 288-42-6 DaY
PubChem[1][2] 9255
Jmol-3D slike Slika 1
Svojstva
Molekulska formula C3H3NO
Molarna masa 69.06 g mol−1
Gustina 1.050 g/cm3
Tačka ključanja

69-70 °C

Baznost (pKb) 0.8

 DaY (šta je ovo?)   (verifikuj)

Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala

Infobox references

Oksazol je osnova velike klase heterocikličnih aromatičnih organskih jedinjenja. Oni su azoli kod kojih su kiseonik i azot odvojeni jednim ugljenikom.[3] Oksazoli su u manjoj meri aromatični od tiazola. Oksazol je slaba baza. Njegova konjugovana kiselina ima pKa od 0.8, u poređenju sa 7 za imidazol.[4][5][6][7]

Priprema

Klasični sintetički metodi oksazola su

The Robinson-Gabriel synthesis
The Robinson-Gabriel synthesis
Fišerova sinteza oksazola
Fišerova sinteza oksazola

Drugi metodi su isto tako poznati.

oxazoline from propargyl amides Merkul 2006
Oxazoline Synthesis Continuous Reactor

Biosinteza

U biomolekulima, oksazoli su proizvod ciklizacije i oksidacije serina ili treonina neribozomskih peptida:

Gde je X = H, CH3 za serin i treonin respektivno, B = baza.
(1) Enzimatska ciklizacija. (2) Eliminacija. (3) [O] = enzimatska oksidacija.

Oksazoli su manje zastupljeni u biomolekulima od srodnih tiazola.

Reference

  1. ↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  edit
  2. ↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1. 
  3. ↑ Heterocyclic Chemistry TL Gilchrist, The Bath press 1985 ISBN 0-582-01421-2
  4. ↑ Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882. 
  5. ↑ Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6. 
  6. ↑ McMurry John E. (1992). Fundamentals of Organic Chemistry (3rd izd.). Belmont: Wadsworth. ISBN 0-534-16218-5. 
  7. ↑ Morrison Robert Thornton, Boyd Robert Neilson (2006). Organic chemistry. Engelwood Cliffs, New Jersey: Prentice Hall. ISBN 8120307658. 
  8. ↑ Robinson, R. J. Chem. Soc. 1909, 95, 2167.
  9. ↑ Gabriel, S. Chemische Berichte 1910, 43, 134.
  10. ↑ Gabriel, S. Chemische Berichte 1910, 43, 1283.
  11. ↑ Emil Fischer, Chemische Berichte 1896, 29, 205.
  12. ↑ Wiley, R. H. Chem. Rev. 1945, 37, 401.
  13. ↑ A new consecutive three-component oxazole synthesis by an amidation–coupling–cycloisomerization (ACCI) sequence, Eugen Merkul and Thomas J. J. Müller, Chem. Commun., 2006, 4817 - 4819, DOI:10.1039/b610839c
  14. ↑ Fully Automated Continuous Flow Synthesis of 4,5-Disubstituted Oxazoles Marcus Baumann, Ian R. Baxendale, Steven V. Ley, Christoper D. Smith, and Geoffrey K. Tranmer, Org. Lett.; 2006; 8(23) pp 5231 - 5234; (Letter) DOI:10.1021/ol061975c

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