2,7-bis-ethinyl-bicyclo<4.4.1>undeca-1,3,5,7,9-pentaen | 134956-24-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2,7-bis-ethinyl-bicyclo<4.4.1>undeca-1,3,5,7,9-pentaen
• 英文别名: 2,7-diethynylbicyclo[4.4.1]undeca-1,3,5,7,9-pentaene
• CAS: 134956-24-4
• 化学式: C₁₅H₁₀
• 分子量: 190.244
• InChiKey: VFNPZUDFQMOOCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  2,7-dibromo-1,6-methano[10]annulene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide sodium hydroxide 、 二乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2,7-bis-ethinyl-bicyclo<4.4.1>undeca-1,3,5,7,9-pentaen
  参考文献：
  名称：

  Synthesen und Eigenschaften ethinylierter und trimethylsilylethinylierter Molek�lsysteme mit 1,6-Methano[10]annulen-Partialstruktur

  摘要：

  2-Trimethylsilylethinylated 1,6-methano[10]annulene 1 a was obtained by reaction of 2-bromo-1,6-methano[10]annulene with trimethylsilylacetylene in the presence of bis-(triphenylphosphin-)-Pd (II) chloride and Cu(I) and also by reaction of 1,1-diiodo-2-(1,6-methano[10]annulene-2-yl)-ethene (2) with n-buthyl-lithium followed by hydrolysis. 1 a reacts with 2N NaOH to 2-ethinyl-1,6-methano[10]annulene (1 b). 2,7- and 2, 10-dibromo-1,6-methano[10]annulene can be substituted to give the trimethylsilylethinylated compounds 3 a-6 a, which then can be transformed with 2N NaOH into the desilylated products 3 b-5 b.

  DOI：

  10.1007/bf00809363

文献信息

• NEIDLEIN, RICHARD;WINKLER, RALF, MONATSH. CHEM., 122,(1991) N, C. 177-184
  作者：NEIDLEIN, RICHARD、WINKLER, RALF

  DOI：——

  日期：——
• Synthesen und Eigenschaften ethinylierter und trimethylsilylethinylierter Molek�lsysteme mit 1,6-Methano[10]annulen-Partialstruktur
  作者：Richard Neidlein、Ralf Winkler

  DOI：10.1007/bf00809363

  日期：1991.3

  2-Trimethylsilylethinylated 1,6-methano[10]annulene 1 a was obtained by reaction of 2-bromo-1,6-methano[10]annulene with trimethylsilylacetylene in the presence of bis-(triphenylphosphin-)-Pd (II) chloride and Cu(I) and also by reaction of 1,1-diiodo-2-(1,6-methano[10]annulene-2-yl)-ethene (2) with n-buthyl-lithium followed by hydrolysis. 1 a reacts with 2N NaOH to 2-ethinyl-1,6-methano[10]annulene (1 b). 2,7- and 2, 10-dibromo-1,6-methano[10]annulene can be substituted to give the trimethylsilylethinylated compounds 3 a-6 a, which then can be transformed with 2N NaOH into the desilylated products 3 b-5 b.