Pirazin

Pirazin
	Pyrazine
Drugi nazivi	1,4-Diazabenzen, p-Diazin, 1,4-Diazin, Paradiazin, Piazin, UN 1325
Identifikacija
CAS registarski broj	290-37-9
PubChem	9261
ChemSpider	8904
EINECS broj	206-027-6
ChEBI	30953
Jmol-3D slike	Slika 1
SMILES
	c1cnccn1
InChI
	InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H ; Kod: KYQCOXFCLRTKLS-UHFFFAOYSA-N InChI=1/C4H4N2/c1-2-6-4-3-5-1/h1-4H
Svojstva
Molekulska formula	C4H4N2
Molarna masa	80.09 g/mol
Agregatno stanje	Beli kristali
Gustina	1.031 g/cm3
Tačka topljenja	52 °C
Tačka ključanja	115 °C
Rastvorljivost u vodi	Rastvorljiv je
pKa	0.37
Opasnost
NFPA 704	2 2 0
R-oznake	R11, R36/37/38
S-oznake	S16, S26, S36
Tačka paljenja	55 °C c.c.
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Pirazin je heterociklično aromatično organsko jedinjenje.^[5]

Pirazin je simetričan molekul. Njegovi derivati kao što je fenazin su poznati po njihovoj antitumorskoj, antibiotskoj i diuretičkoj aktivnosti. Pirazin je manje bazan od piridina, piridazina i pirimidina. Tetrametilpirazin (ligustrazin) se zna da sakuplja anjone superoksida i umanjuje produkciju azot oksida u ljudskim leukocitima^[6]. Tetrametilpirazin je takođe komponenta nekih medicinskih biljaka^[7].

Sinteza uredi

Postoji više metoda za organsku sintezu pirazina i njegovih derivata.

U Staedel-Rugheimerovoj sintezi pirazina (1876) 2-hloroacetofenon reaguje sa amonijakom do amino ketona, zatim se kondenzuje i oksidira u purazin^[8] Varijacija tog metoda je Gutknečtova sinteza pirazina (1879), koja je takođe bazirana na samokondenzaciji, ali se razlikuje u načinu sinteze alfa-ketoamina^[9]^[10]

Vidi još uredi

Literatura 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.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.
↑ Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882.
↑ Zhang Z, Wei T, Hou J, Li G, Yu S, Xin W (April 2003). „Tetramethylpyrazine scavenges superoxide anion and decreases nitric oxide production in human polymorphonuclear leukocytes”. Life Sci. 72 (22): 2465–72. PMID 12650854.
↑ „ligustrazine”.
↑ W. Staedel, L. Rügheimer (1876). „Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol”. Berichte der deutschen chemischen Gesellschaft 9 (1): 563-564. DOI:10.1002/cber.187600901174.
↑ H. Gutknecht (1879). „Mittheilungen Ueber Nitrosoäthylmethylketon”. Berichte der deutschen chemischen Gesellschaft 12 (2): 2290 - 2292. DOI:10.1002/cber.187901202284.
↑ T.L. Gilchrist. Heterocyclic chemistry. ISBN 0-582-01421-2.

Spoljašnje veze uredi

Portal Hemija

Bezbednosni podaci Arhivirano 2007-10-11 na Wayback Machine-u
Bezbednosna evaluacija prehrambenih aditiva

[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] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., Determination of Organic Structures by Physical Methods, Academic Press, New York, 1955.

[Katritzky2nd-5] Katritzky A.R., Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry. Academic Press. ISBN 0080429882.

[pmid12650854-6] Zhang Z, Wei T, Hou J, Li G, Yu S, Xin W (April 2003). „Tetramethylpyrazine scavenges superoxide anion and decreases nitric oxide production in human polymorphonuclear leukocytes”. Life Sci. 72 (22): 2465–72. PMID 12650854.

[7] „ligustrazine”.

[8] W. Staedel, L. Rügheimer (1876). „Ueber die Einwirkung von Ammoniak auf Chloracetylbenzol”. Berichte der deutschen chemischen Gesellschaft 9 (1): 563-564. DOI:10.1002/cber.187600901174.

[9] H. Gutknecht (1879). „Mittheilungen Ueber Nitrosoäthylmethylketon”. Berichte der deutschen chemischen Gesellschaft 12 (2): 2290 - 2292. DOI:10.1002/cber.187901202284.

[10] T.L. Gilchrist. Heterocyclic chemistry. ISBN 0-582-01421-2.

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