(Z)-2,3,3,4,4,5,5,6,6,7,7-Undecafluoro-1-iodo-hept-1-ene | 672339-40-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-2,3,3,4,4,5,5,6,6,7,7-Undecafluoro-1-iodo-hept-1-ene
• 英文别名: (Z)-2,3,3,4,4,5,5,6,6,7,7-undecafluoro-1-iodohept-1-ene
• CAS: 672339-40-1
• 化学式: C₇H₂F₁₁I
• 分子量: 421.98
• InChiKey: TYYCSLBFNGPIQR-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (Z)-2,3,3,4,4,5,5,6,6,7,7-Undecafluoro-1-iodo-hept-1-ene 以52%的产率得到
  参考文献：
  名称：

  YAMANAKA HIROKI; ARAKI TAKAYUKI; KUWABARA MASAKI; FUKUNISHI KOUSHI; NOMUR+, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1986) N 10, 1321-1328

  摘要：

  DOI：
• 作为产物：
  描述：

  1H,1H,7H-碘代十二氟庚酯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 (Z)-2,3,3,4,4,5,5,6,6,7,7-Undecafluoro-1-iodo-hept-1-ene
  参考文献：
  名称：

  Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives

  摘要：

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01199-2

文献信息

• YAMANAKA HIROKI; ARAKI TAKAYUKI; KUWABARA MASAKI; FUKUNISHI KOUSHI; NOMUR+, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1986) N 10, 1321-1328
  作者：YAMANAKA HIROKI、 ARAKI TAKAYUKI、 KUWABARA MASAKI、 FUKUNISHI KOUSHI、 NOMUR+

  DOI：——

  日期：——
• Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives
  作者：Tsutomu Konno、Jungha Chae、Masashi Kanda、Go Nagai、Kazushige Tamura、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/s0040-4020(03)01199-2

  日期：2003.9

  Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2 equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2.TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh3)(4), reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields. (C) 2003 Elsevier Ltd. All rights reserved.