扭曲烷

扭曲烷
	IUPAC名; tricyclo[4.4.0.03,8]decane; 三环[4.4.0.03,8]癸烷
别名	扭烷; 异三环癸烷
识别
CAS号	253-14-5 ; 37165-27-8 ; 21449-14-9
PubChem	5460768
ChemSpider	4574225, 34984822, 34984821
SMILES	C1CC2CC3CCC2CC13;
InChI	1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2;
Beilstein	1919499; 2232311
ChEBI	32904
性质
化学式	C10H16
摩尔质量	136.23 g·mol−1
熔点	163-164.8 °C（436-438 K）
结构
配位几何	D2
偶极矩	0 D
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

扭曲烷（英語：Twistane），又称异三环癸烷，是一种有机化合物，化学式为C₁₀H₁₆。^[2]它是一种环烷烃，也是金刚烷最简单的同分异构体。与金刚烷类似，其挥发性不强。扭曲烷的名称来源于其結構被强行扭曲成环己烷构象（俗稱“扭船型”）。^[3]該化合物由Whitlock於1962年首次發現。^[4]

合成[编辑]

扭曲烷已经有多种合成路线。1962年最初的方法是基于双环[2.2.2]辛烷框架。^[4]1967年发表的一篇文章涉及顺式萘烷二酮的分子内（英语：intramolecular reaction）羟醛缩合反应。^[5]篮烷催化加氢可以制得扭曲烷。^[6]^[可疑]

对称性[编辑]

扭曲烷的唯一对称操作是旋转，其存在3个二重轴。因此，扭曲烷的点群为D₂。尽管扭曲烷有四个立构中心，但是它只存在两种对映异构体。这是因为其沿着自身C₂对称轴对称。^[7]

聚扭曲烷[编辑]

聚扭曲烷是一種假想的稠合扭曲烷單元聚合物，有待實際合成。^[8]^[9]^[10]^[11]

参考资料[编辑]

^ Quinkert, Gerhard; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard, Aspects of Organic Chemistry: Structure, Basel, Switzerland: Helvetica Chimica Acta: 107, 1996 [2008-12-09], ISBN 3-906390-15-2
^ Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Henning Hopf ISBN 978-3-527-29606-4. 2000
^ Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd, Organic Chemistry, Horwood Publishing: 416, 1997 [2008-12-09], ISBN 1-898563-37-3
^ ^4.0 ^4.1 Tricyclo[4.4.0.03.8]Decane H. W. Whitlock Journal of the American Chemical Society 1962 84 (17), 3412-3413 doi:10.1021/ja00876a047
^ A new synthesis of twistane Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, doi:10.1139/v67-052
^ Ho, Tse-Lok, Symmetry: A Basis for Synthesis Design, Wiley-IEEE: 69, 1995 [2008-12-10], ISBN 0-471-57376-0
^ Kalsi, P. S., Stereochemistry Conformation and Mechanism, New Age Publishers: 94, 2005 [2008-12-10], ISBN 81-224-1564-4
^ Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R., Trauner, D. and Allen, W. D. (2014), Polytwistane. Chem. Eur. J., 20: 1638–1645. doi:10.1002/chem.201303081
^ A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane Martin Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112 doi:10.1039/C3OB42152J
^ Synthetic Studies toward Polytwistane Hydrocarbon Nanorods Martin Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 doi:10.1021/jo502618g
^ Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods Boris Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026 doi:10.1021/ct5011505

[asp-1] Quinkert, Gerhard; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard, Aspects of Organic Chemistry: Structure, Basel, Switzerland: Helvetica Chimica Acta: 107, 1996 [2008-12-09], ISBN 3-906390-15-2

[hopf-2] Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Henning Hopf ISBN 978-3-527-29606-4. 2000

[bw-3] Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd, Organic Chemistry, Horwood Publishing: 416, 1997 [2008-12-09], ISBN 1-898563-37-3

[whitlock-4] 4.0 ^4.1 Tricyclo[4.4.0.03.8]Decane H. W. Whitlock Journal of the American Chemical Society 1962 84 (17), 3412-3413 doi:10.1021/ja00876a047

[Deslongchamps-5] A new synthesis of twistane Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, doi:10.1139/v67-052

[sym-6] Ho, Tse-Lok, Symmetry: A Basis for Synthesis Design, Wiley-IEEE: 69, 1995 [2008-12-10], ISBN 0-471-57376-0

[ste-7] Kalsi, P. S., Stereochemistry Conformation and Mechanism, New Age Publishers: 94, 2005 [2008-12-10], ISBN 81-224-1564-4

[Barua-8] Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R., Trauner, D. and Allen, W. D. (2014), Polytwistane. Chem. Eur. J., 20: 1638–1645. doi:10.1002/chem.201303081

[Mayer-9] A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane Martin Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112 doi:10.1039/C3OB42152J

[olbrich-10] Synthetic Studies toward Polytwistane Hydrocarbon Nanorods Martin Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 doi:10.1021/jo502618g

[Maryasin-11] Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods Boris Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026 doi:10.1021/ct5011505

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