四氢硒吩

四氢硒吩是一种有机硒化合物，化学式为C₄H₈Se。它需要在充氮的棕色瓶中保存。^[4]

四氢硒吩
别名	硒杂环戊烷
识别
CAS号	3465-98-3  Y
SMILES	Se1CCCC1
性质
化学式	C4H8Se
摩尔质量	135.07 g·mol−1
外观	黄色油状液体
密度	1.4715 g·cm−3[1]
沸点	141.4 °C（414.5 K）[2]
溶解性（水）	0.02 g（25 °C）[3]
相关物质
其他阴离子	四氢呋喃 四氢噻吩 四氢碲吩
相关化学品	硒吩
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成

四氢硒吩可由灰硒和1,4-二溴丁烷为原料反应制得。硒和甲醛次硫酸氢钠在碱性溶液中反应，得到硒化钠，它再和1,4-二溴丁烷反应，得到产物。^[4]硒化物也可选用硒化钾，它可由硒、氢氧化钾和水合肼反应得到。^[5]需要注意反应需要隔绝氧气，否则硒化钠会被氧化为多硒化钠，产物中会带有二硒代环己烷等杂质。^[4]

反应

四氢硒吩和二氯化硒或二溴化硒反应在有机溶剂中反应，可以得到它的二卤化物，同时析出红硒：^[6]

它和五氯化铌、镁在二氯甲烷中反应，可以得到配合物[{NbCl₂(THSe)}₂(μ-Cl)₂(μ-THSe)]。^[7]它和内盐C₆H₅I-C(NO₂)₂反应，可以得到C₄H₈Se-C(NO₂)₂。^[8]它和1-碘丁烷反应，可以得到1-丁基四氢硒吩碘化物。^[9]

参考文献

1. Yur'ev, Yu. K. Catalytic transformations of heterocyclic compounds. XX. Transformations of heterocycles containing oxygen into heterocycles containing selenium. Zhurnal Obshchei Khimii, 1946. 16. 851-854. ISSN: 0044-460X. CODEN: ZOKHA4.
2. Milazzo, Giulio. Absorption spectra of heterocyclic compounds. VII. Spectra of saturated derivatives: tetrahydro-N-methylpyrrole, tetrahydrothiophene, and tetrahydroselenophene. Rend. ist. super, sanita, 1959. 22: 479-494. CAN54: 60529.
3. Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2021 ACD/Labs). Retrieved from SciFinder. [2021-07-10].
4. Junk, T; Gritzner, G; Irgolic, K J. Improved Preparation of Tetrahydroselenophene (Selenacyclopentane) and Tetrahydroteliajrophene (Tellur Acy Clopentane). Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 1989, 19 (9): 931–936. ISSN 0094-5714. doi:10.1080/00945718908050645.
5. Levanova, E. P.; Grabel’nykh, V. A.; Elaev, A. V.; Russavskaya, N. V.; Klyba, L. V.; Albanov, A. I.; Korchevin, N. A. Novel route to the synthesis of chalcogenolanes, chalcogenanes, and 1,2-dichalcogenaepanes*. Chemistry of Heterocyclic Compounds. 2012, 47 (11): 1345–1352. ISSN 0009-3122. doi:10.1007/s10593-012-0920-7.
6. Potapov, Vladimir A.; Amosova, Svetlana V.; Abramova, Elena V.; Musalov, Maxim V.; Lyssenko, Konstantin A.; Finn, M. G. 2,6-Dihalo-9-selenabicyclo[3.3.1]nonanes and their complexes with selenium dihalides: synthesis and structural characterisation. New Journal of Chemistry. 2015, 39 (10): 8055–8059. ISSN 1144-0546. doi:10.1039/C5NJ00684H.
7. Matsuura, Masatoshi; Fujihara, Takashi; Kakeya, Masaki; Sugaya, Tomoaki; Nagasawa, Akira. Dinuclear niobium(III) and tantalum(III) complexes with thioether and selenoether ligands [{MIIIX2(L)}2(μ-X)2(μ-L)] (M = Nb, Ta; X = Cl, Br; L = R2S, R2Se): Syntheses, structures, and the optimal conditions and the mechanism of the catalysis for regioselective cyclotrimerization of alkynes. Journal of Organometallic Chemistry. 2013,. 745-746: 288–298. ISSN 0022-328X. doi:10.1016/j.jorganchem.2013.07.035.
8. Semenov, V. V.; Mel'nikova, L. G.; Shevelev, S. A.; Fainzil'berg, A. A. Nitroylides. Communication 7. Synthesis of alkyl-substituted selenonium nitroylides and some of their reactions（俄文）. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980. 1: 138-144. ISSN: 0002-3353. CODEN: IASKA6.
9. Hawker, Rebecca R.; Haines, Ronald S.; Harper, Jason B. Rational selection of the cation of an ionic liquid to control the reaction outcome of a substitution reaction. Chemical Communications. 2018, 54 (18): 2296–2299. ISSN 1359-7345. doi:10.1039/C8CC00241J.

拓展阅读

• Noyori, R. et al. Science of Synthesis, 39: Category 5, Compounds with One Saturated Carbon Heteroatom Bond – Product Subclass 4: Cyclic DIalkyl Selenoxides and Derivatives. 2008. doi:10.1055/sos-SD-039-01388.