Nonacyclo[28.2.2.26,9.214,17.222,25.02,29.05,10.013,18.021,26]tetraconta-2(29),5(10),13(18),21(26)-tetraen-3,11,19,27-tetrayne | 178958-93-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: Nonacyclo[28.2.2.26,9.214,17.222,25.02,29.05,10.013,18.021,26]tetraconta-2(29),5(10),13(18),21(26)-tetraen-3,11,19,27-tetrayne
• CAS: 178958-93-5
• 化学式: C₄₀H₄₀
• 分子量: 520.758
• InChiKey: JDOPGAVEFYWJAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  silver trifluoromethanesulfonate 、 Nonacyclo[28.2.2.26,9.214,17.222,25.02,29.05,10.013,18.021,26]tetraconta-2(29),5(10),13(18),21(26)-tetraen-3,11,19,27-tetrayne 以 四氢呋喃 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Synthesis and structural characterization of novel silver(i) complexes of tetradehydro[16]annulene annelated with bicyclo[2.2.2]octene units

  摘要：

  制备了第一个由双环[2.2.2]辛烯单元环化的四氢[16]环烯的银（I）配合物，并通过X射线晶体学证实了银原子被引入空腔中心。

  DOI：

  10.1039/a806606j
• 作为产物：
  描述：

  2,3-dibromobicyclo(2.2.2)oct-2-ene 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 PhCH₃NEt₃Cl 作用下， 以 水 、 二乙胺 、 苯 为溶剂， 反应 34.0h， 生成 Nonacyclo[28.2.2.26,9.214,17.222,25.02,29.05,10.013,18.021,26]tetraconta-2(29),5(10),13(18),21(26)-tetraen-3,11,19,27-tetrayne
  参考文献：
  名称：

  Synthesis, Structure, and Redox Behavior of the Dehydroannulenes Fused with Bicyclo[2.2.2]octene Frameworks

  摘要：

  Two series of dehydroannulenes fused with bicyclo[2.2.2]octene (BCO) units were synthesized either by an oxidative coupling with copper(I) under air or by a palladium-copper-catalyzed coupling. The first series of dehydroannulenes consisted of tetradehydro[l2]annulene (12), hexadehydro[l8]annulene (13), octadehydro[24]annulene (14), and decadehydro[30]annulene (15), which all have the BCO units connected by the butadiyne linkage. The second consisted of tridehydro[12]annulene (16) and tetradehydro[16]annulene (17), which have the BCO units connected by the acetylene bond. The molecular structures of the relatively stable annulenes 13 and 17 were determined by X-ray crystallography, which showed that 13 has a planar ct-system, whereas 17 has a tub structure like cyclooctatetraene. The H-1 NMR signal for the bridgehead proton of the BCO units is a good measure for the ring current effect. This signal clearly indicated the presence of diatropicity in [18]annulene 13 and paratropicity in [12]annulenes 12 and 16. The redox properties of these annulenes were examined by cyclic voltammetry. The antiaromatic [12]- and [16]annulenes 18 and la having only one acetylene bond between the BCO units were found to be more readily oxidized than the other annulenes as expected from the energy level of HOMOs calculated by the PM3 semiempirical MO method.

  DOI：

  10.1021/jo9705531

文献信息

• Synthesis, Structure, and Redox Behavior of the Dehydroannulenes Fused with Bicyclo[2.2.2]octene Frameworks
  作者：Tohru Nishinaga、Tetsu Kawamura、Koichi Komatsu

  DOI：10.1021/jo9705531

  日期：1997.8.1

  Two series of dehydroannulenes fused with bicyclo[2.2.2]octene (BCO) units were synthesized either by an oxidative coupling with copper(I) under air or by a palladium-copper-catalyzed coupling. The first series of dehydroannulenes consisted of tetradehydro[l2]annulene (12), hexadehydro[l8]annulene (13), octadehydro[24]annulene (14), and decadehydro[30]annulene (15), which all have the BCO units connected by the butadiyne linkage. The second consisted of tridehydro[12]annulene (16) and tetradehydro[16]annulene (17), which have the BCO units connected by the acetylene bond. The molecular structures of the relatively stable annulenes 13 and 17 were determined by X-ray crystallography, which showed that 13 has a planar ct-system, whereas 17 has a tub structure like cyclooctatetraene. The H-1 NMR signal for the bridgehead proton of the BCO units is a good measure for the ring current effect. This signal clearly indicated the presence of diatropicity in [18]annulene 13 and paratropicity in [12]annulenes 12 and 16. The redox properties of these annulenes were examined by cyclic voltammetry. The antiaromatic [12]- and [16]annulenes 18 and la having only one acetylene bond between the BCO units were found to be more readily oxidized than the other annulenes as expected from the energy level of HOMOs calculated by the PM3 semiempirical MO method.
• Synthesis and structural characterization of novel silver(i) complexes of tetradehydro[16]annulene annelated with bicyclo[2.2.2]octene units
  作者：Tohru Nishinaga、Tetsu Kawamura、Koichi Komatsu

  DOI：10.1039/a806606j

  日期：——

  The first silver(I) complexes of tetradehydro[16]annulene annelated with bicyclo[2.2.2]octene units were prepared and the incorporation of a silver atom into the cavity center was shown by X-ray crystallography.

  制备了第一个由双环[2.2.2]辛烯单元环化的四氢[16]环烯的银（I）配合物，并通过X射线晶体学证实了银原子被引入空腔中心。