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Revision as of 14:43, 12 November 2010 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: StdInChI StdInChIKey.		Latest revision as of 13:41, 3 August 2023 edit Arado Ar 196 (talk | contribs)Extended confirmed users10,053 edits fixed ref
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	{{Chembox		{{Chembox
	| verifiedrevid = 389070272		| verifiedrevid = 396324541
	| Name = Decene		| Name = 1-Decyne
	| ImageFile1 = 1-decene.svg		| ImageFile1 = 1-Decyne.svg
			| ImageFile2 = <math chem>\scriptstyle\ce{CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-C#CH}</math>
	| ImageSize1 = 280px
			| ImageSize2 = 300px
	| ImageFile2 = Dec-1-ene.svg
			| PIN = Dec-1-yne
	| ImageSIze2 = 280px
			| OtherNames = 1-Decyne
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
⚫	| ChemSpiderID = 12809
		⚫	| CASNo_Ref = {{cascite|changed|CAS}}
⚫	| InChI = 1/C10H20/c1-3-5-7-9-10-8-6-4-2/h3H,1,4-10H2,2H3
		⚫	| CASNo = 764-93-2
	| InChIKey = AFFLGGQVNFXPEV-UHFFFAOYAO
			| ChEBI = 87322
⚫	| StdInChI = 1S/C10H20/c1-3-5-7-9-10-8-6-4-2/h3H,1,4-10H2,2H3
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| StdInChIKey = AFFLGGQVNFXPEV-UHFFFAOYSA-N
		⚫	| ChemSpiderID = 12456
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| InChI = 1/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3
⚫	| CASNo = 872-05-9
			| InChIKey = ILLHQJIJCRNRCJ-UHFFFAOYAE
	| SMILES = CCCCCCCCC=C
		⚫	| StdInChI = 1S/C10H18/c1-3-5-7-9-10-8-6-4-2/h1H,4-10H2,2H3
		⚫	| StdInChIKey = ILLHQJIJCRNRCJ-UHFFFAOYSA-N
			| PubChem = 12997
			| EC_number = 212-132-8
			| UNII = ULR28GD98Q
			| UNII_Ref = {{fdacite|correct|FDA}}
			| SMILES = C(#C)CCCCCCCC
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=10 | H=18
	| Formula = C<sub>10</sub>H<sub>20</sub>
			| Appearance = Colorless liquid
	| Density = 0,741 g/cm<sup>3</sub> {{Citation needed|date=July 2010}}
			| Density = 0.767 g/cm<sup>3</sup>
	| MeltingPt = 207,2 ] (-66.0 °C) {{Citation needed|date=July 2010}}
			| MeltingPtC = -44
	| BoilingPt = 445,2 ] (172.0 °C) {{Citation needed|date=July 2010}}
			| BoilingPtC = 174
⚫	}}
			| RefractIndex = 1.426–1.428
⚫	| Section8 = {{Chembox Related
		⚫	}}
	| Function = ]s
			|Section7={{Chembox Hazards
	| OtherFunctn = ]<br />]<br />]<br />]
			| ExternalSDS =
⚫	| OtherCpds = ]<br />]
			| NFPA-H =
			| NFPA-F =
			| NFPA-R =
			| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}{{GHS09}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|226|315|318|335|410}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|362|370+378|391|403+233|403+235|405|501}}
			| FlashPtC = 48
			| AutoignitionPtC =
			}}
		⚫	|Section8={{Chembox Related
			| OtherFunction_label = ]s
			| OtherFunction = Octyne<br />Nonyne<br />Undecyne<br />Dodecyne
		⚫	| OtherCompounds = ]<br />]<br />]
	}}		}}
	}}		}}
	'''Decene''' is an ] with the formula C<sub>10</sub>H<sub>20</sub>. the molecular weight is 140.26 g/mol. Decene has ten carbon atoms in its parent chain and contains a double bond. It has 20 hydrogen atoms. This article will address decene as the specific constitutional isomer, 1-decene, as well as the broader scope of all possible unsubstituted decenes.
			'''1-Decyne''' is the ] with the formula C<sub>8</sub>H<sub>17</sub>C≡CH. It is a ]. A colorless liquid, 1-decyne is used as a model substrate when evaluating methodology in ]. It participates in a number of classical reactions including ]s, ]s,<ref>{{cite journal |doi=10.1002/anie.200502017|title=General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water|year=2005|last1=Anderson|first1=Kevin W.|last2=Buchwald|first2=Stephen L.|journal=Angewandte Chemie International Edition|volume=44|issue=38|pages=6173–6177|pmid=16097019}}</ref> ]s,<ref>{{cite journal |doi=10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4|title=A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes|year=2002|last1=Rostovtsev|first1=Vsevolod V.|last2=Green|first2=Luke G.|last3=Fokin|first3=Valery V.|last4=Sharpless|first4=K. Barry|journal=Angewandte Chemie International Edition|volume=41|issue=14|pages=2596–2599|pmid=12203546}}</ref> and ]s.<ref>{{cite journal |doi=10.1021/ja00076a081|title=Platinum(0)-Catalyzed Diboration of Alkynes|year=1993|last1=Ishiyama|first1=Tatsuo|last2=Matsuda|first2=Nobuo|last3=Miyaura|first3=Norio|last4=Suzuki|first4=Akira|journal=Journal of the American Chemical Society|volume=115|issue=23|pages=11018–11019}}</ref>
	This molecule would be more correctly named as Dec-1-ene, or 1-decene. Although, in ], if a numerical value is not present as a description of the ] location, then the first position is indicated. Therefore, Decene would be an ] containing 10 ] atoms, with a double bond between carbon 1 and 2 (the numbering of double bonds is always given as the lowest possible number, so 2-decene would be a double bond between carbon 2 & 3, 3-decene would include a double bond between carbon 3&4, and so on). Decene, being an alkene of 10 carbon atoms, could be 1, 2, 3, 4, or 5-decene - or written with the numerical value placed immediately prior to the suffix, Dec-5-ene (this type of naming, although correct, is generally reserved to situations when the substitution numbering becomes confusing). There are NO 6-decenes, or 7, 8 9 or 10 for that matter, as substituents must ALWAYS have the lowest possible numerical value, and 10-decene is structurally identical to 1-decene. The double bond may also be at the second, third, fourth or fifth position, in which case the numerical value indicating the first carbon involved in the sigma/pi double bond is essential to proper naming. In addition to describing the location of the double bond, with 2-5 decene one would have to describe the ]. 1-decene is the only possible ] of decene that does not exist as a pair of ]. 2-decene, for example, has a double bond between carbon 2 & carbon three, therefore, both carbons are bonded to an alkyl group, and a hydrogen. The pi-bond in a carbon-carbon double bond does not allow for free rotation (which is the case for sigma bonds), so there are two possible orientations. Put very simply, if the alkyl groups (carbon containing substituents) are on the same side of the pi bond, then the compound is said to be a ]. A 2-decene compound containing only cis diastereomers would be named cis-2-decene. If the alkyl groups on either side of the double bond are on opposite sides (one up, one down), then it would be named as a trans-2-decene.
			Under the catalysis of ], it reacts with ] to produce ].<ref>{{cite journal|journal=RSC Advances|volume=2|issue=8|language=en|issn=2046-2069|date=2012|pages=3477|doi=10.1039/c2ra01097f|url=http://xlink.rsc.org/?DOI=c2ra01097f|title=Controlled hydrogenation of aromatic compounds by platinum nanowire catalysts|accessdate=2021-11-16|author1=Zhiqiang Guo|author2=Lei Hu|author3=Hsiao-hua Yu|author4=Xueqin Cao|author5=Hongwei Gu|bibcode=2012RSCAd...2.3477G}}</ref>
			==See also==
	Decene, being a mono-unsaturated hydrocarbon will have the chemical formula C<sub>n</sub>H<sub>2n</sub>. This basic relationship is true for all monounsaturated hydrocarbons, and for all saturated monocyclic hydrocarbons. In ], the ratio of carbons to hydrogens is C<sub>n</sub>H<sub>n+2</sub>.
			* ]
			==References==
	1-Decene, or any other decene, can be produced in several different ways, but almost all routes involve an elimination as the final step. To produce 1-decene there is a minor obstacle to synthesis, as this is a mono-substituted alkene, the least stable of alkenes. Generally, elimination will favor more substituted products when possible. To avoid the more substituted product (the ]), and obtain the ], in this care a mono-substituted product, the most common method would be the use of a very "bulky" base, such as (CH<sub>3</sub>)<sub>3</sub>CO<sup>-</sup>K<sup>+</sup> , potassium tert-butoxide. The concept behind this synthesis is that the tertiary butyl group possesses simply too much space to overcome the ] necessary to abstract a hydrogen from one of the secondary carbons. Generally, an elimination of a compound such as 2-bromodecane with potassium t-butoxide would result in the t-butoxide abstraction of a hydrogen (H<sup>+</sup>)from the primary carbon, the electrons that formerly formed the bond between the primary carbon and the proton would migrate to the p-orbital of the primary carbon, and overlap with the secondary carbon number 2. These electrons would cause the bond between carbon 2 and the bromine atom to sever (as bromine is an excellent leaving group), resulting in 1-decene, and Br<sup>-</sup>K<sup>+</sup>. Reactions of this variety usually result in 50-60% Hoffman product (1-decene).
			{{reflist}}
			{{Alkynes}}
	The next possible synthesis method would include hydrogenation of 1-decyne, the 1-alkyne ] of decene. The reaction could be a syn-addition of hydrogen, with Ni<sub>2</sub>B (aka P-2 catalyst) as a catalyst. Another catalyst that stops hydrogenation at the alkene is ], which produces a syn-addition product. The distinction between syn and anti is not significant in the synthesis of 1-decene as there are two hydrogens on the 1 carbon.
			{{Hydrocarbons}}
			{{Hydrides by group}}
			{{DEFAULTSORT:Decyne, 1-}}
	For the synthesis of 2-decene, use of the above catalysts with 2-decyne would yield cis-2-decene. Liquid ammonia and sodium reduction would result in the trans-2 product.
		⚫	]
			]
⚫	]
			{{hydrocarbon-stub}}
	]
	]
	]
	]
	]