維基百科

5-溴-1-戊烯

化合物

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]

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  checkY
SMILES
 
  • C=CCCCBr
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。

製備

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

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

  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. 
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