房烷

房烷
	IUPAC名; Bicyclo[2.1.0]pentane
别名	双环[2.1.0]戊烷
识别
CAS号	185-94-4
PubChem	9101
ChemSpider	8747
SMILES	C1C2CCC12;
InChI	1/C5H8/c1-2-5-3-4(1)5/h4-5H,1-3H2;
InChIKey	MHLPKAGDPWUOOT-UHFFFAOYAN
性质
化学式	C5H8
摩尔质量	68.12 g·mol−1
外观	无色液体
沸点	45.5 °C
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

房烷（英語：Housane）是一种饱和的双环烷烃，化学式为C₅H₈。在室温下为无色挥发性液体。它的名字“房烷”来源于像房子的形状。在结构上，该分子由与环丁烷稠合的环丙烷组成。

制备

房烷可以由2,3-二氮双环[2.2.1]庚-2-烯的热分解而成。这个方法是鲁道夫·克里奇（英语：Rudolf Criegee）在1957年发表的。^[2]^[3]

它也可以由2,3-二氮双环[2.2.1]庚-2-烯的光分解，N-苯基-2-氧-3-氮双环[2.2.1]庚烷的热分解或是甲烯加成到环丁烯而成。^[4]^[5]^[6]^[7]

性质

房烷很容易被溴或碘攻击。在铂催化剂下，房烷在室温下就会被氢化成环戊烷。它和溴化氢在低温下反应产生的是溴代环戊烷。房烷和四乙酸铅反应则生成cis-1,3-二(乙酰氧基)环戊烷。^[2]

房烷对热稳定，330 °C才异构化成环戊烯。^[2](Rh(CO)₂Cl)₂可以催化房烷异构化成环戊烯的反应，室温下的反应半衰期为8小时。^[8]

另見

名稱獨特的化學物質列表

参考资料

^ P. G. Gassman, K. T. Mansfield, Bicyclo[2.1.0]pentane, Organic Syntheses 49, 1969, 49: 1, doi:10.15227/orgsyn.049.0001
^ ^2.0 ^2.1 ^2.2 Rudolf Criegee, Annemarie Rimmelin, Darstellung und Eigenschaften von Bicyclo-[0.1.2]-Pentan, Chemische Berichte 90 (3), 1957, 90 (3): 414–417, doi:10.1002/cber.19570900319
^ Saul G. Cohen, Robert Zand, Colin Steel, Preparation and Kinetics of Decomposition of a Bicyclic Azo Compound. A Novel Reduction¹, Journal of the American Chemical Society 83 (13), 1961, 83 (13): 2895, doi:10.1021/ja01474a025
^ Colin Steel, Photolysis of Bicyclic Aza Compounds. I. 2,3-Diazabicyclo[2.2.1]2-heptene, The Journal of Physical Chemistry 67 (9), 1963, 67 (9): 1779–1781, doi:10.1021/j100803a008
^ Timothy F. Thomas, Colin Steel, Photoinitiation of Unimolecular Reactions. The Photolysis of 2,3-Diazabicyclo[2.2.1]hept-2-ene, Journal of the American Chemical Society 87 (23), 1965, 87 (23): 5290, doi:10.1021/ja00951a005
^ C. E. Griffin, N. F. Hepfinger, B. L. Shapiro, The Pyrolysis of 2-Phenyltetrahydro-1,2-oxazines as a Simple Preparative Entry to Cyclobutanes, Journal of the American Chemical Society 85 (17), 1963, 85 (17): 2683, doi:10.1021/ja00900a049
^ Georg Wittig, Frank Wingler, Über methylenierte Metallhalogenide, IV. Cyclopropan-Bildung aus Olefinen mit Bis-halogenmethyl-zink, Chemische Berichte 97 (8), 1964-08, 97 (8): 2146, doi:10.1002/cber.19640970808
^ Gassman, Paul; Atkins, Thomas; Lumb, J. Transition Metal Complex Promoted Rearrangements. Bicyclo[2.1.0]pentane and 1-Carbomethoxybicyclo[2.1.0]pentane. Journal of the American Chemical Society (American Chemical Society (ACS)). 1972, 94 (22): 7757–7761. ISSN 0002-7863. doi:10.1021/ja00777a604.

[Gassman-1] P. G. Gassman, K. T. Mansfield, Bicyclo[2.1.0]pentane, Organic Syntheses 49, 1969, 49: 1, doi:10.15227/orgsyn.049.0001

[RCriegee-2] 2.0 ^2.1 ^2.2 Rudolf Criegee, Annemarie Rimmelin, Darstellung und Eigenschaften von Bicyclo-[0.1.2]-Pentan, Chemische Berichte 90 (3), 1957, 90 (3): 414–417, doi:10.1002/cber.19570900319

[3] Saul G. Cohen, Robert Zand, Colin Steel, Preparation and Kinetics of Decomposition of a Bicyclic Azo Compound. A Novel Reduction¹, Journal of the American Chemical Society 83 (13), 1961, 83 (13): 2895, doi:10.1021/ja01474a025

[4] Colin Steel, Photolysis of Bicyclic Aza Compounds. I. 2,3-Diazabicyclo[2.2.1]2-heptene, The Journal of Physical Chemistry 67 (9), 1963, 67 (9): 1779–1781, doi:10.1021/j100803a008

[5] Timothy F. Thomas, Colin Steel, Photoinitiation of Unimolecular Reactions. The Photolysis of 2,3-Diazabicyclo[2.2.1]hept-2-ene, Journal of the American Chemical Society 87 (23), 1965, 87 (23): 5290, doi:10.1021/ja00951a005

[6] C. E. Griffin, N. F. Hepfinger, B. L. Shapiro, The Pyrolysis of 2-Phenyltetrahydro-1,2-oxazines as a Simple Preparative Entry to Cyclobutanes, Journal of the American Chemical Society 85 (17), 1963, 85 (17): 2683, doi:10.1021/ja00900a049

[7] Georg Wittig, Frank Wingler, Über methylenierte Metallhalogenide, IV. Cyclopropan-Bildung aus Olefinen mit Bis-halogenmethyl-zink, Chemische Berichte 97 (8), 1964-08, 97 (8): 2146, doi:10.1002/cber.19640970808

[8] Gassman, Paul; Atkins, Thomas; Lumb, J. Transition Metal Complex Promoted Rearrangements. Bicyclo[2.1.0]pentane and 1-Carbomethoxybicyclo[2.1.0]pentane. Journal of the American Chemical Society (American Chemical Society (ACS)). 1972, 94 (22): 7757–7761. ISSN 0002-7863. doi:10.1021/ja00777a604.

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