8-hexyl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-(7E)-buten-9-yne | 329697-99-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 8-hexyl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-(7E)-buten-9-yne
• 英文别名: (E)-2-hexyl-1-perfluorohexyl-1-buten-3-yne；(E)-8-ethynyl-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorotetradec-7-ene
• CAS: 329697-99-6
• 化学式: C₁₆H₁₅F₁₃
• 分子量: 454.274
• InChiKey: ALMJLUNCMXACLN-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  8-hexyl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-(7E)-buten-9-yne 在 bis(1,5-cyclooctadiene)nickel (0) 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到1,2,4-tris(1-hexyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-(1E)-octenyl)benzene
  参考文献：
  名称：

  Highly Regioselective Cyclotrimerization of 1-Perfluoroalkylenynes Catalyzed by Nickel

  摘要：

  We report the highly regioselective cyclotrimerization of the 1-perfluoroalkylenynes in the presence of Ni(PPh3)(4). The substituent effects on the reactivity of the enynes were investigated. We also succeeded in the nickel-catalyzed cocyclization of the 1-perfluoroalkylenynes with (trimethylsilyl)acetylene. The possible structures of the intermediates of the cyclotrimerization and the reasons for the observed high regioselectivity were discussed.

  DOI：

  10.1021/jo0056242
• 作为产物：
  描述：

  1-辛炔 在 四(三苯基膦)钯 potassium fluoride 、 copper(l) iodide 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 3.17h， 生成 8-hexyl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-(7E)-buten-9-yne
  参考文献：
  名称：

  Highly Regioselective Cyclotrimerization of 1-Perfluoroalkylenynes Catalyzed by Nickel

  摘要：

  We report the highly regioselective cyclotrimerization of the 1-perfluoroalkylenynes in the presence of Ni(PPh3)(4). The substituent effects on the reactivity of the enynes were investigated. We also succeeded in the nickel-catalyzed cocyclization of the 1-perfluoroalkylenynes with (trimethylsilyl)acetylene. The possible structures of the intermediates of the cyclotrimerization and the reasons for the observed high regioselectivity were discussed.

  DOI：

  10.1021/jo0056242

文献信息

• Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3 + 2 + 2] Cocyclization. Application to the Synthesis of Polycyclic Compounds
  作者：Shinsuke Komagawa、Kouhei Takeuchi、Ikuo Sotome、Isao Azumaya、Hyuma Masu、Ryu Yamasaki、Shinichi Saito

  DOI：10.1021/jo900189g

  日期：2009.5.1

  The nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and conjugated enynes proceeded smoothly and divinylcycloheptadienes were isolated in high yields. The three-component cocyclization of ethyl cyclopropylideneacetate, conjugated enynes, and (trimethylsilyl)acetylene also proceeded in a highly selective manner to afford vinylcycloheptadienes, which were reacted with various

  镍催化的环丙基亚乙基乙酸乙酯和共轭烯炔的[3 + 2 + 2]环加成反应进展顺利，并且高收率分离出了二乙烯基环庚二烯。环亚丙基乙酸乙酯，共轭烯炔和（三甲基甲硅烷基）乙炔的三组分共环化也以高度选择性的方式进行，得到乙烯基环庚二烯，其与各种亲二烯体反应。这项研究提供了一种新的，短步合成具有环庚烷骨架的多环化合物的方法。