5-溴-1-戊烯
外觀
5-溴-1-戊烯 | |
---|---|
英文名 | 5-Bromo-1-pentene |
別名 | 5-溴戊-1-烯 1-溴-4-戊烯 |
識別 | |
CAS號 | 1119-51-3 |
SMILES |
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性質 | |
化學式 | C5H9Br |
莫耳質量 | 149.03 g·mol⁻¹ |
密度 | 1.2581 g·cm−3[1] |
沸點 | 125—126 °C(398—399 K)[2] |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
5-溴-1-戊烯是一種有機化合物,化學式為C5H9Br,它可用作有機合成試劑。[3]
製備
[編輯]5-溴-1-戊烯可由4-戊烯-1-醇和四溴化碳在三苯基膦的存在下反應製得,[4]反應所需的溴化劑也可選擇三溴化磷:[5]
反應原料也可以使用價格較低的1,5-二溴戊烷。[6]1,5-二甲基戊烷在加熱下和六甲基磷醯胺反應,可以得到5-溴-1-戊烯。[6]
1,5-二甲基戊烷在叔丁醇鉀等強鹼作用下也能轉化為5-溴-1-戊烯。[7]
反應
[編輯]5-溴-1-戊烯和三苯基膦反應,生成4-戊烯基三苯基溴化鏻[8];和1-甲基咪唑反應,得到相應的咪唑季銨鹽:[9]
在碳酸鉀存在下,它和苯硫酚在N,N-二甲基甲醯胺中反應,生成苯基(4-戊烯基)硫醚;[10]和4-硝基苯酚在乙腈反應,生成相應的醚[11]。
它和碘化鈉在丙酮中反應,得到5-碘-1-戊烯;[12]和硫氰酸鉀在乙醇中反應,得到4-戊烯基硫氰酸酯。[13]
參考文獻
[編輯]- ^ Levina, R. Ya.; Viktorova, E. A. Synthesis of hydrocarbons. XIX. Synthesis and contact isomerization of 1,7-octadiene. Vestnik Moskovskogo Universiteta, 1951. 6-1 (2): 89-92. ISSN: 0372-6320.
- ^ Kharasch, M. S.; Fuchs, Charles F. THE CONVERSION OF QUATERNARY PYRROLIDINIUM SALTS TO OPEN-CHAIN DIAMINES. The Journal of Organic Chemistry. 1944, 09 (4): 359–372. ISSN 0022-3263. doi:10.1021/jo01186a008.
- ^ van Heyningen, E. The Perkin Synthesis of Five- and Six-membered Rings. Journal of the American Chemical Society. 1954, 76 (8): 2241–2243. ISSN 0002-7863. doi:10.1021/ja01637a065.
- ^ Simocko, Chester; Young, Thomas C.; Wagener, Kenneth B. ADMET Polymers Containing Precisely Spaced Pendant Boronic Acids and Esters. Macromolecules. 2015, 48 (16): 5470–5473. ISSN 0024-9297. doi:10.1021/acs.macromol.5b01410.
- ^ Xie, Yinjun; Qian, Bo; Xie, Pan; Huang, Hanmin. Cooperative Catalysis with Aldehydes and Copper: Development and Application in Aerobic Oxidative C-H Amination at Room Temperature. Advanced Synthesis & Catalysis. 2013, 355 (7): 1315–1322. ISSN 1615-4150. doi:10.1002/adsc.201200944.
- ^ 6.0 6.1 Kraus, George A.; Landgrebe, Kevin. A Direct Synthesis of ω-Bromo-1-alkenes. Synthesis. 1984, 1984 (10): 885–885. ISSN 0039-7881. doi:10.1055/s-1984-31010.
- ^ Baughman, Travis W.; Sworen, John C.; Wagener, Kenneth B. The facile preparation of alkenyl metathesis synthons. Tetrahedron. 2004, 60 (48): 10943–10948. ISSN 0040-4020. doi:10.1016/j.tet.2004.09.021.
- ^ Chu, Qianli; Makhlouf Brahmi, Malika; Solovyev, Andrey; Ueng, Shau-Hua; Curran, Dennis P.; Malacria, Max; Fensterbank, Louis; Lacôte, Emmanuel. Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes. Chemistry - A European Journal. 2009, 15 (47): 12937–12940. ISSN 0947-6539. doi:10.1002/chem.200902450.
- ^ Corberán, Rosa; Sanaú, Mercedes; Peris, Eduardo. “Cp*Ir(III)” Complexes with Hemicleaveable Ligands of the TypeN-Alkenyl Imidazolin-2-ylidene. Reactivity and Catalytic Properties. Organometallics. 2007, 26 (14): 3492–3498. ISSN 0276-7333. doi:10.1021/om070188w.
- ^ Horn, Alissa; Dussault, Patrick H. Synthesis of α-Cyano and α-Sulfonyl Cyclic Ethers via Intramolecular Reactions of Peroxides with Sulfone- and Nitrile-Stabilized Carbanions. The Journal of Organic Chemistry. 2019, 84 (22): 14611–14626. ISSN 0022-3263. doi:10.1021/acs.joc.9b02112.
- ^ Wang, Xiaojun; Wu, Yongming. Direct oxidative isoperfluoropropylation of terminal alkenes via hexafluoropropylene (HFP) and silver fluoride. Chemical Communications. 2018, 54 (15): 1877–1880. ISSN 1359-7345. doi:10.1039/C7CC07614B.
- ^ Spiegel, Jochen; Cromm, Philipp M.; Itzen, Aymelt; Goody, Roger S.; Grossmann, Tom N.; Waldmann, Herbert. Direct Targeting of Rab-GTPase-Effector Interactions. Angewandte Chemie International Edition. 2014, 53 (9): 2498–2503. ISSN 1433-7851. doi:10.1002/anie.201308568.
- ^ Piva, Olivier; Cros, Fanny; Pelotier, Béatrice. Microwave-Assisted Cross-Metathesis of Unsaturated Thiocyanates: Application to the Synthesis of Thiocyanatins A and B and Analogues. Synthesis. 2009, 2010 (02): 233–238. ISSN 0039-7881. doi:10.1055/s-0029-1217089.