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Revision as of 17:17, 15 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit		Latest revision as of 13:02, 5 December 2024 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,468 edits cite
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			{{short description|Chemical compound}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 401973266
			| verifiedrevid = 414091056
	| Name = Cyclooctane
			| Name = Cyclooctane
	| ImageFile1 = Regular octagon.svg
			| ImageFile1_Ref = {{chemboximage|correct|??}}
	| ImageSize1 = 120px
			| ImageFile =
	| ImageFileL2 = cyclooctane_ballandstick.png
			| ImageFile1 = Regular octagon.svg
	| ImageSizeL2 = 120px
			| ImageSize1 = 120px
	| ImageFileR2 = Cyclooctane_spacefilling.png
			| ImageAlt1 = Skeletal formula
	| ImageSizeR2 = 120px
			| OtherNames = Cyclo-octane
	| Section1 = {{Chembox Identifiers
			| IUPACName =
	| SMILES = C1CCCCCCC1
			| PIN = Cyclooctane
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| SystematicName =
			| Section1 = {{Chembox Identifiers
			| SMILES = C1CCCCCCC1
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 8909		| ChemSpiderID = 8909
	| PubChem = 9266		| PubChem = 9266
	| InChI = 1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2		| InChI = 1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2
	| InChIKey = WJTCGQSWYFHTAC-UHFFFAOYAO		| InChIKey = WJTCGQSWYFHTAC-UHFFFAOYAO
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 452651		| ChEMBL = 452651
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 292-64-8		| CASNo = 292-64-8
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = KKZ3KBS654
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| Formula =
	| Formula = ''']'''<sub>8</sub>''']'''<sub>16</sub>
			| C=8 | H=16
	| MolarMass = 112.21 g/mol
	| Density = 0.834 g/cm<sup>3</sup>		| Density = 0.840 g/cm<sup>3</sup><ref name="ECHA REACH">ECHA REACH</ref>
	| Solubility = 7.90 mg/L		| Solubility = 7.90 mg/L
			| MeltingPtC = 14.5 | MeltingPt_ref= <ref name="ECHA REACH"/>
	| MeltingPt = 14.59 °C
			| BoilingPtC = 151.2 | BoilingPt_ref= <ref name="ECHA REACH"/>
	| BoilingPt = 149 °C
			| MagSus = −91.4·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
			| Section3 =
	| Section8 = {{Chembox Related
			| Section4 =
	| Function = ]s
			| Section5 =
	| OtherFunctn = ]
			| Section6 =
			| Section8 = {{Chembox Related
			| OtherFunction_label = ]s
			| OtherFunction = ]
	}}		}}
	}}		}}
			'''Cyclooctane''' is a ] with the ] (CH<sub>2</sub>)<sub>8</sub>.<ref name="Mackay" /> It is a simple colourless ], but it is often a reference compound for saturated eight-membered ring compounds in general.
			Cyclooctane has a ]aceous odor.<ref>{{cite journal |author=Sell, C. S. |title=On the Unpredictability of Odor |journal=Angew. Chem. Int. Ed. |volume=45 |issue=38 |pages=6254–6261 |year=2006 |doi=10.1002/anie.200600782 |pmid=16983730}}</ref>
	'''Cyclooctane''' is a ] with the ] (CH<sub>2</sub>)<sub>8</sub>.<ref name=Mackay>{{cite book
	| last =Mackay
	| first =Donald
	| authorlink =
	| coauthors =
	| title =Handbook of Physical-chemical Properties and Environmental Fate for Organic Chemicals
	| publisher =CRC Press
	| date =2006
	| location =
	| url =http://books.google.com/?id=wjd-nEugVskC
	| doi =
	| id =
	| isbn = 1566706874
	| page =258}}</ref> It is a simple colourless ], but it is often a reference compound for saturated eight-membered ring compounds in general.
	==Conformation==		==Conformations==
			{{Details|Macrocyclic stereocontrol#Cyclooctane}}
	The ] has been studied extensively using ] methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy." The boat-chair conformation '''I''' is the most stable form.<ref name=Hendrickson1967>{{Cite journal
			The ] of cyclooctane has been studied extensively using ] methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form.<ref name="Hendrickson1967" /> This conformation was confirmed by Allinger and co-workers.<ref name="Dorofeeva1985" /> The crown conformation (below)<ref name="IUPAC_Crown" /> is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S<sub>8</sub>, elemental ].
	| last = Hendrickson
	| first = James B.
	| title = Molecular Geometry V. Evaluation of Functions and Conformations of Medium Rings
	| journal = ]
	| volume = 89
	| issue = 26
	| pages = 7036–7043
	| year = 1967
	| doi = 10.1021/ja01002a036
	| postscript = <!--None--> }}</ref> This conformation was confirmed by Allinger and co-workers.<ref name=Dorofeeva1985>{{cite journal
	| author = Dorofeeva, O.V.
	| coauthors = Mastryukov, V.S.; Allinger, N.L.; Almenningen, A.
	| year = 1985
	| title = The molecular structure and conformation of cyclooctane as determined by electron diffraction and molecular mechanics calculations
	| journal = The Journal of Physical Chemistry
	| volume = 89
	| issue = 2
	| pages = 252–257
	| url = http://pubs.acs.org/doi/pdf/10.1021/j100248a015
	| accessdate = 2008-02-05
	| doi = 10.1021/j100248a015
	| format =
	}}</ref> The crown conformation<ref name=IUPAC_Crown>{{GoldBookRef|title=crown conformation|file=C01422}}</ref> '''II''' is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S<sub>8</sub>, elemental ].
			: {|class="wikitable" style="text-align: center;"
	:] {{clear-left}}
			|+
			|]
			|]
			|]
			|]
			|-
			| colspan="2" |Boat-chair<ref name=":0">{{Cite journal |last1=Pakes |first1=P. W. |last2=Rounds |first2=T. C. |last3=Strauss |first3=H. L. |date=1981 |title=Conformations of cyclooctane and some related oxocanes |journal=The Journal of Physical Chemistry |volume=85 |issue=17 |pages=2469–2475 |doi=10.1021/j150617a013 |issn=0022-3654}}</ref>
			| colspan="2" |Crown<ref name=":0" />
			|-
			|]
			|]
			|]
			|]
			|-
			|Tub<ref>{{Cite journal |last=Moss |first=G. P. |date=1996 |title=Basic terminology of stereochemistry (IUPAC Recommendations 1996) |url=http://iupac.org/publications/pac/68/12/2193/ |journal=Pure and Applied Chemistry |volume=68 |issue=12 |pages=2193–2222 |doi=10.1351/pac199668122193 |s2cid=98272391 |issn=0033-4545|doi-access=free }}</ref>
			|Boat-boat<ref name=":0" />
			|Twist boat-chair<ref name=":0" />
			|Twist chair-chair<ref name=":0" />
			|}
	==Synthesis and reactions==		==Synthesis and reactions==
	The main route to cyclooctane derivatives involves the dimerization of ], catalysed by nickel(0) complexes such as ].<ref>Thomas Schiffer, Georg Oenbrink “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.{{DOI|10.1002/14356007.a08_205}}</ref> This process affords, among other products, 1,5-] (COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for ]. The activation of these catalysts under H2, produces cyclooctane, which is usually discarded or burnt:		The main route to cyclooctane derivatives involves the dimerization of ], catalysed by nickel(0) complexes such as ].<ref name="thomas" /> This process affords, among other products, ] (COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for ]. The activation of these catalysts under H<sub>2</sub>, produces cyclooctane, which is usually discarded or burnt:
	:C<sub>8</sub>H<sub>12</sub> + 2 H<sub>2</sub> → C<sub>8</sub>H<sub>16</sub>		:C<sub>8</sub>H<sub>12</sub> + 2 H<sub>2</sub> → C<sub>8</sub>H<sub>16</sub>
	Cyclooctane participates in no reactions except those typical of a other saturated hydrocarbons, ] and ]. Recent work on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.<ref>{{cite journal|last=Deng|first=Guojun|coauthors=Wenwen Chen, Chao-Jun Li|date=February 2009|title=An Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes|journal=Advanced synthesis & catalysis|volume=351|pages=353–356|doi=10.1002/adsc.200800689}}</ref>		Cyclooctane participates in no reactions except those typical of other saturated hydrocarbons, ] and ]. Work in 2009 on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.<ref name="deng" />
	:] {{clear-left}}		:] {{Clear left}}
	==References==		==References==
	{{reflist}}		{{reflist|refs=
			<ref name="Mackay">{{Cite book
			| last =Mackay
			| first =Donald
			| authorlink =
			| title =Handbook of Physical-chemical Properties and Environmental Fate for Organic Chemicals
			| publisher =CRC Press
			| year =2006
			| url =https://books.google.com/books?id=wjd-nEugVskC
			| isbn = 978-1-56670-687-2
			| page =258
			}}</ref>
			<ref name="Hendrickson1967">{{Cite journal
			| last = Hendrickson
			| first = James B.
			| title = Molecular Geometry V. Evaluation of Functions and Conformations of Medium Rings
			| journal = ]
			| volume = 89
			| issue = 26
			| pages = 7036–7043
			| year = 1967
			| doi = 10.1021/ja01002a036
			}}</ref>
			<ref name="thomas">Thomas Schiffer, Georg Oenbrink, “Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a08_205}}.</ref>
			<ref name="Dorofeeva1985">{{cite journal
			| author = Dorofeeva, O. V. |author2=Mastryukov, V. S. |author3=Allinger, N. L. |author4=Almenningen, A.
			| year = 1985
			| title = The molecular structure and conformation of cyclooctane as determined by electron diffraction and molecular mechanics calculations
			| journal = The Journal of Physical Chemistry
			| volume = 89
			| issue = 2
			| pages = 252–257
			| doi = 10.1021/j100248a015
			}}</ref>
			<ref name="IUPAC_Crown">{{GoldBookRef|title=crown conformation|file=C01422}}</ref>
			<ref name="deng">{{Cite journal |last=Deng |first=Guojun |author2=Wenwen Chen |author3=Chao-Jun Li |date=February 2009 |title=An Unusual Peroxide-Mediated Amination of Cycloalkanes with Nitroarenes |journal=Advanced Synthesis & Catalysis |volume=351 |issue=3 |pages=353–356 |doi=10.1002/adsc.200800689}}</ref>
			}}
	{{cycloalkanes}}		{{cycloalkanes}}
			{{Authority control}}
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]