Benzofuran

Benzofuran
	1-Benzofuran
Drugi nazivi	Kumaron, benzo[b]furan
Identifikacija
CAS registarski broj	271-89-6
PubChem	9223
ChemSpider	8868
UNII	LK6946W774
DrugBank	DB04179
KEGG	C14512
ChEBI	35260
ChEMBL	CHEMBL363614
Jmol-3D slike	Slika 1
SMILES
	o2c1ccccc1cc2
InChI
	InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H ; Kod: IANQTJSKSUMEQM-UHFFFAOYSA-N InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H; Kod: IANQTJSKSUMEQM-UHFFFAOYAU
Svojstva
Molekulska formula	C8H6O
Molarna masa	118.13 g mol−1
Tačka topljenja	-18 °C, 255 K, -0 °F
Tačka ključanja	173 °C, 446 K, 343 °F
Opasnost
LD50	500 mg/kg (mice).
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Benzofuran je heterociklično jedinjenje koji se sastoji od kondenzovanih prstena benzena i furana. Ova bezbojna tečnost je komponenta katrana. Benzofuran je osnova mnogih srodnih jedinjenja sa kompleksnijim strukturama. Na primer, psoralen je derivat benzofurana koji se javlja u nekoliko biljki.

Produkcija

Benzofuran se može ekstrahovati iz katrana. On se takođe dobija dehidrogenacijom 2-etilfenola.^[6]

Laboratorijski metodi

Benzofuran se može pripremiti putem O-alkilacije salicilaldehida sa hlorosirćetnom kiselinom i naknadnom dehidratacijom nastalog etra.^[7] U drugom metodu zvanom Perkinovo preuređenje^[8]^[9]^[10] kumarin reaguje sa hidroksidom:

Srodna jedinjenja

Reference

↑ 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
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ ^6,0 ^6,1 Collin, G.; Höke, H. (2007). „Benzofurans”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. DOI:10.1002/14356007.l03_l01.
↑ Burgstahler, A. W.; Worden, L. R. (1966), „Coumarone”, Organic Syntheses 46: 28 ; Coll. Vol. 5: 251
↑ Perkin, W. H. (1870). „XXIX. On some New Bromine Derivatives of Coumarin”. Journal of the Chemical Society 23: 368–371. DOI:10.1039/JS8702300368.
↑ Perkin, W. H. (1871). „IV. On some New Derivatives of Coumarin”. Journal of the Chemical Society 24: 37–55. DOI:10.1039/JS8712400037.
↑ Bowden, K.; Battah, S. (1998). „Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement”. Journal of the Chemical Society, Perkin Transactions 2 1998 (7): 1603–1606. DOI:10.1039/a801538d.

Spoljašnje veze

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] 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] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[Ullmann-6] 6,0 ^6,1 Collin, G.; Höke, H. (2007). „Benzofurans”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. DOI:10.1002/14356007.l03_l01.

[7] Burgstahler, A. W.; Worden, L. R. (1966), „Coumarone”, Organic Syntheses 46: 28 ; Coll. Vol. 5: 251

[8] Perkin, W. H. (1870). „XXIX. On some New Bromine Derivatives of Coumarin”. Journal of the Chemical Society 23: 368–371. DOI:10.1039/JS8702300368.

[9] Perkin, W. H. (1871). „IV. On some New Derivatives of Coumarin”. Journal of the Chemical Society 24: 37–55. DOI:10.1039/JS8712400037.

[10] Bowden, K.; Battah, S. (1998). „Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement”. Journal of the Chemical Society, Perkin Transactions 2 1998 (7): 1603–1606. DOI:10.1039/a801538d.

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