5-溴-1-戊烯

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5-溴-1-戊烯
英文名 5-Bromo-1-pentene
别名 5-溴戊-1-烯
1-溴-4-戊烯
识别
CAS号 1119-51-3  ✓
SMILES
性质
化学式 C5H9Br
摩尔质量 149.03 g·mol⁻¹
密度 1.2581 g·cm−3[1]
沸点 125~126 °C(398~399 K)[2]
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

5-溴-1-戊烯是一种有机化合物,化学式为C5H9Br,它可用作有机合成试剂。[3]

制备[编辑]

5-溴-1-戊烯可由4-戊烯-1-醇和四溴化碳三苯基膦的存在下反应制得,[4]反应所需的溴化剂也可选择三溴化磷[5]

5-bromo-1-pentene synthesis (CBr4).png
5-bromo-1-pentene synthesis (PBr3).png

反应原料也可以使用价格较低的1,5-二溴戊烷德语1,5-Dibrompentan[6]1,5-二甲基戊烷在加热下和六甲基磷酰胺反应,可以得到5-溴-1-戊烯。[6]

5-bromo-1-pentene synthesis (HMPT).png

1,5-二甲基戊烷在叔丁醇钾等强碱作用下也能转化为5-溴-1-戊烯。[7]

反应[编辑]

5-溴-1-戊烯和三苯基膦反应,生成4-戊烯基三苯基溴化𬭸[8];和1-甲基咪唑反应,得到相应的咪唑季铵盐[9]

5-bromo-1-pentene + 1-methylimidazole.png

碳酸钾存在下,它和苯硫酚N,N-二甲基甲酰胺中反应,生成苯基(4-戊烯基)硫醚;[10]4-硝基苯酚乙腈反应,生成相应的醚[11]

它和碘化钠丙酮中反应,得到5-碘-1-戊烯;[12]硫氰酸钾乙醇中反应,得到4-戊烯基硫氰酸酯。[13]

参考文献[编辑]

  1. ^ 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.
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ 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.