1,5-Ciklooktadien

1,5-Ciklooktadien
Naziv po klasifikaciji	Ciklookta-1,5-dien
Identifikacija
Abrevijacija	1,5-COD
CAS registarski broj	111-78-4 , 1552-12-1 (1Z,5Z)-1,5-diene, 5259-71-2 (1Z,5E)-1,5-diene, 17612-50-9 (1E,5E)-1,5-diene
PubChem	8135, ; 10937607 (5Z)-5-ene, ; 82916 (1Z,5Z)-1,5-diene, ; 5364364 (1Z,5E)-1,5-diene, ; 5702534 (1E,5E)-1,5-diene
ChemSpider	7843 , 74815 (1Z,5Z)-1,5-diene , 18520443 (1Z,5E)-1,5-diene , 19971660 (1E,5E)-1,5-diene
EINECS broj	203-907-1
UN broj	2520
MeSH	1,5-cyclooctadiene
RTECS registarski broj toksičnosti	GX9560000; GX9620000 (1Z,5Z)-1,5-diene
Bajlštajn	2036542;
3DMet	(1Z,5Z)-1,5-diene.html 1209288 (1Z,5Z)-1,5-diene
Jmol-3D slike	Slika 1
SMILES
	C1CC=CCCC=C1
InChI
	InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7- ; Kod: VYXHVRARDIDEHS-QGTKBVGQSA-N InChI=1/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-; Kod: VYXHVRARDIDEHS-QGTKBVGQBM
Svojstva
Molekulska formula	C8H12
Molarna masa	108.18 g mol−1
Agregatno stanje	bezbojna tačnost
Gustina	882 mg cm-3
Tačka topljenja	-69 °C, 204 K, -92 °F
Tačka ključanja	150 °C, 423 K, 302 °F
Napon pare	910 Pa
Indeks prelamanja (nD)	1,493
Termohemija
Standardna entalpija stvaranja jedinjenja ΔfHo298	21-27 kJ mol-1
Std entalpija; sagorevanja ΔcHo298	-4.890--4.884 MJ mol-1
Standardna molarna entropija So298	250.0 J K-1 mol-1
Specifični toplotni kapacitet, C	198.9 J K-1 mol-1
Opasnost
EU-klasifikacija	Xn
R-oznake	R10, R36/38, R42/43, R65
S-oznake	S23, S26, S36/37, S62
Tačka paljenja	32-38 °C
Tačka spontanog paljenja	222 °C
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

1,5-Ciklooktadien (skr. COD) je organsko jedinjenje sa hemijskom formulom C₈H₁₂. Ovaj dien je koristan prekurzor drugih organskih jedinjenja i služi kao ligand u organometalnoj hemiji.^[5]^[6]

Sinteza

1,5-Ciklooktadien se može pripremiti dimerizacijom butadiena u prisustvu nikl katalizator. Nusproizvod je vinilcikloheksen. Aproksimativno 10,000 tona je proizvedeno 2005.^[7]

Organske reakcije

COD reaguje sa borom i daje 9-borabiciklo[3.3.1]nonan,^[8] koji je poznat kao 9-BBN. Ovaj reagens se koristi u organskoj hemiji u hidroboraciji:

COD dodaje SCl₂ (ili slične reagense) i daje 2,6-dihloro-9-thiabiciklo[3.3.1]nonan:^[9]

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, synthesis and reactions

Rezultirajući dihlorid se može dalje modifikovati kao di-azid ili di-cijano derivat u nukleofilnoj supstituciji.

Literatura

↑ „AC1L1QCE - Compound Summary”. PubChem Compound. USA: National Center for Biotechnology Information. 26. 3. 2005.. Identification and Related Records. Pristupljeno 14. 10. 2011.
↑ 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
↑ Buehler, C; Pearson, D.Survey of Organic Syntheses. Wiley-Intersciene, New York. 1970.

↑ Shriver, D; Atkins, P.Inorganic Chemistry. W. H. Freeman and Co., New York. 1999.

↑ Thomas Schiffer, Georg Oenbrink “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.

↑ John A. Soderquist and Alvin Negron (1998), „9-Borabicyclo[3.3.1]nonane Dimer”, Organic Syntheses; Coll. Vol. 9: 95

↑ Roger Bishop, „9-Thiabicyclo[3.3.1]nonane-2,6-dione”, Organic Syntheses; Coll. Vol. 9: 692Díaz, David Díaz; Converso, Antonella; Sharpless, K. Barry; Finn, M. G. (2006). „2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold”. Molecules 11 (4): 212–218. DOI:10.3390/11040212.

Spoljašnje veze

Portal Hemija

1,5-Ciklooktadien

[1] „AC1L1QCE - Compound Summary”. PubChem Compound. USA: National Center for Biotechnology Information. 26. 3. 2005.. Identification and Related Records. Pristupljeno 14. 10. 2011.

[2] 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

[3] 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.

[4] 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

[buehler-5] Buehler, C; Pearson, D.Survey of Organic Syntheses. Wiley-Intersciene, New York. 1970.

[shriver-6] Shriver, D; Atkins, P.Inorganic Chemistry. W. H. Freeman and Co., New York. 1999.

[thomas-7] Thomas Schiffer, Georg Oenbrink “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.

[john-8] John A. Soderquist and Alvin Negron (1998), „9-Borabicyclo[3.3.1]nonane Dimer”, Organic Syntheses ; Coll. Vol. 9: 95

[bishop-9] Roger Bishop, „9-Thiabicyclo[3.3.1]nonane-2,6-dione”, Organic Syntheses ; Coll. Vol. 9: 692 Díaz, David Díaz; Converso, Antonella; Sharpless, K. Barry; Finn, M. G. (2006). „2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold”. Molecules 11 (4): 212–218. DOI:10.3390/11040212.

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p r u Cikloalkeni
Alkeni	Ciklopropen • Ciklobuten • Ciklopenten • Cikloheksen • Ciklohepten • Ciklookten
Dieni	Ciklobutadien • Ciklopentadien • Cikloheksadien (1,3-Cikloheksadien • 1,4-Cikloheksadien) • Cikloheptadien • Ciklooktadien (1,5-Ciklooktadien)