扭曲烷
| 扭曲烷 | |||
|---|---|---|---|
| |||
| IUPAC名 tricyclo[4.4.0.03,8]decane[1] 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 |
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| InChI |
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| 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（英语：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结构被强行扭曲成环己烷构象（俗称“扭船型”）。[3]该化合物由Whitlock于1962年首次发现。[4]
合成
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
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
参考资料
- ^ 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
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