房烷

房烷
	IUPAC名; Bicyclo[2.1.0]pentane
別名	雙環[2.1.0]戊烷
識別
CAS號	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
性質
化學式	C5H8
摩爾質量	68.12 g·mol−1
外觀	無色液體
沸點	45.5 °C
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

房烷（英語：Housane）是一種飽和的雙環烷烴，化學式為C₅H₈。在室溫下為無色揮發性液體。它的名字「房烷」來源於像房子的形狀。在結構上，該分子由與環丁烷稠合的環丙烷組成。

製備

房烷可以由2,3-二氮雙環[2.2.1]庚-2-烯的熱分解而成。這個方法是魯道夫·克里奇（英語：Rudolf Criegee）在1957年發表的。^[2]^[3]

它也可以由2,3-二氮雙環[2.2.1]庚-2-烯的光分解，N-苯基-2-氧-3-氮雙環[2.2.1]庚烷的熱分解或是甲烯加成到環丁烯而成。^[4]^[5]^[6]^[7]

性質

房烷很容易被溴或碘攻擊。在鉑催化劑下，房烷在室溫下就會被氫化成環戊烷。它和溴化氫在低溫下反應產生的是溴代環戊烷。房烷和四乙酸鉛反應則生成cis-1,3-二(乙醯氧基)環戊烷。^[2]

房烷對熱穩定，330 °C才異構化成環戊烯。^[2](Rh(CO)₂Cl)₂可以催化房烷異構化成環戊烯的反應，室溫下的反應半衰期為8小時。^[8]

另見

名稱獨特的化學物質列表

參考資料

^ 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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