Oksazol

Oksazol
	1,3-oxazole
Identifikacija
CAS registarski broj	288-42-6
PubChem	9255
Jmol-3D slike	Slika 1
SMILES
	C1=COC=N1
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
	(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 uredi

Klasični sintetički metodi oksazola su

2

Drugi metodi su isto tako poznati.

2

Biosinteza uredi

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 uredi

↑ 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
↑ 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.
↑ Heterocyclic Chemistry TL Gilchrist, The Bath press 1985 ISBN 0-582-01421-2
↑ Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882.
↑ Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
↑ McMurry John E. (1992). Fundamentals of Organic Chemistry (3rd izd.). Belmont: Wadsworth. ISBN 0-534-16218-5.
↑ Morrison Robert Thornton, Boyd Robert Neilson (2006). Organic chemistry. Engelwood Cliffs, New Jersey: Prentice Hall. ISBN 8120307658.
↑ Robinson, R. J. Chem. Soc. 1909, 95, 2167.
↑ Gabriel, S. Chemische Berichte 1910, 43, 134.
↑ Gabriel, S. Chemische Berichte 1910, 43, 1283.
↑ Emil Fischer, Chemische Berichte 1896, 29, 205.
↑ Wiley, R. H. Chem. Rev. 1945, 37, 401.
↑ 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
↑ 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

Spoljašnje veze uredi

Portal Hemija

[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

[Katritzky2nd-4] Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882.

[Clayden1st-5] Clayden Jonathan, Nick Greeves, Stuart Warren, Peter Wothers (2001). Organic chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.

[McMurry3rd-6] McMurry John E. (1992). Fundamentals of Organic Chemistry (3rd izd.). Belmont: Wadsworth. ISBN 0-534-16218-5.

[MorrisonBoyd6th-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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