扭曲烷

扭曲烷
	IUPAC名; tricyclo[4.4.0.03,8]decane; 三環[4.4.0.03,8]癸烷
別名	扭烷; 異三環癸烷
識別
CAS號	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
性質
化學式	C10H16
摩爾質量	136.23 g·mol−1
熔點	163-164.8 °C（436-438 K）
結構
配位幾何	D2
偶極矩	0 D
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

扭曲烷（英語：Twistane），又稱異三環癸烷，是一種有機化合物，化學式為C₁₀H₁₆。^[2]它是一種環烷烴，也是金剛烷最簡單的同分異構體。與金剛烷類似，其揮發性不強。扭曲烷的名稱來源於其結構被強行扭曲成環己烷構象（俗稱「扭船型」）。^[3]該化合物由Whitlock於1962年首次發現。^[4]

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合成

扭曲烷已經有多種合成路線。1962年最初的方法是基於雙環[2.2.2]辛烷框架。^[4]1967年發表的一篇文章涉及順式萘烷二酮的分子內（英語：intramolecular reaction）羥醛縮合反應。^[5]籃烷催化加氫可以製得扭曲烷。^[6]^[可疑]

對稱性

扭曲烷的唯一對稱操作是旋轉，其存在3個二重軸。因此，扭曲烷的點群為D₂。儘管扭曲烷有四個立構中心，但是它只存在兩種對映異構體。這是因為其沿着自身C₂對稱軸對稱。^[7]

聚扭曲烷

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]

參考資料

[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
[2]
Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Henning Hopf ISBN 978-3-527-29606-4. 2000
[3]
Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd, Organic Chemistry, Horwood Publishing: 416, 1997 [2008-12-09], ISBN 1-898563-37-3
[4]
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
[5]
A new synthesis of twistane Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, doi:10.1139/v67-052
[6]
Ho, Tse-Lok, Symmetry: A Basis for Synthesis Design, Wiley-IEEE: 69, 1995 [2008-12-10], ISBN 0-471-57376-0
[7]
Kalsi, P. S., Stereochemistry Conformation and Mechanism, New Age Publishers: 94, 2005 [2008-12-10], ISBN 81-224-1564-4
[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
[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
[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
[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

[asp-1] [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] [2]
Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Henning Hopf ISBN 978-3-527-29606-4. 2000

[bw-3] [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]
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] [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] [6]
Ho, Tse-Lok, Symmetry: A Basis for Synthesis Design, Wiley-IEEE: 69, 1995 [2008-12-10], ISBN 0-471-57376-0

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

[Barua-8] [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] [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] [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] [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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