6,9,10,13-tetrakis(dodecyloxy)[7]helicenebisquinone | 215385-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6,9,10,13-tetrakis(dodecyloxy)[7]helicenebisquinone
• 英文别名: 11,16,17,22-tetradodecoxyheptacyclo[16.12.0.02,15.03,12.04,9.021,30.024,29]triaconta-1(18),2(15),3,6,9,11,13,16,19,21,23,26,29-tridecaene-5,8,25,28-tetrone
• CAS: 215385-50-5
• 化学式: C₇₈H₁₁₀O₈
• 分子量: 1175.73
• InChiKey: OBFNEPLQPPWUMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.2
• 重原子数：
  86
• 可旋转键数：
  48
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,9,10,13-tetrakis(dodecyloxy)[7]helicenebisquinone 在 溶剂黄146 、 锌 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes

  摘要：

  Alcohols containing HCl transform the hydroquinone reduction-products of helicenebisquinones into p-alkoxyphenols that have the alkoxyls specifically on the peripheries of the helices. The reactions are quick, and the yields are high. Alkoxyls at the 6-position are replaced also, but only after 2 h at 60 degrees C, not after the 5 min at 25 degrees C sufficient to replace the peripheral hydroxyls of the hydroquinones. After the remaining inside hydroxyls of a dihydroxytetramethoxy[6]helicene prepared by this procedure have been converted into camphanates, one diastereomer crystallizes from solution, allowing an enantiomer resolution to be carried out on a large scale. By then simply reapplying the procedure with alcoholic acid, a variety of resolved dihydroxytetraalkoxy[6]helicenes can be prepared in excellent yields without resolution procedures having to be developed for each, Similar procedures are effective when applied to a [7]carbohelicene.

  DOI：

  10.1021/jo9914972
• 作为产物：
  描述：

  9,10-Bis-(tert-butyl-dimethyl-silanyloxy)-3,6-bis-(1-triisopropylsilanyloxy-vinyl)-phenanthrene 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 88.5h， 生成 6,9,10,13-tetrakis(dodecyloxy)[7]helicenebisquinone
  参考文献：
  名称：

  Efficient Synthesis of Functionalized [7]Helicenes

  摘要：

  [7]Helicenebisquinones can be made easily and in quantity by reacting the silyl enol ethers of a 9,10-dialkoxy-, or better a 9,10-disiloxy-, 3,6-diacetylphenanthrene, with p-benzoquinone. If an ethyl, enol ether is used in place of the silyl enol ether, the transformation proceeds in much lower yield. The [7]helicenes are efficiently resolved into their enantiomers, and absolute configurations are assigned.

  DOI：

  10.1021/jo981380y

文献信息

• Efficient Synthesis of Functionalized [7]Helicenes
  作者：Joseph M. Fox、Naomi R. Goldberg、Thomas J. Katz

  DOI：10.1021/jo981380y

  日期：1998.10.1

  [7]Helicenebisquinones can be made easily and in quantity by reacting the silyl enol ethers of a 9,10-dialkoxy-, or better a 9,10-disiloxy-, 3,6-diacetylphenanthrene, with p-benzoquinone. If an ethyl, enol ether is used in place of the silyl enol ether, the transformation proceeds in much lower yield. The [7]helicenes are efficiently resolved into their enantiomers, and absolute configurations are assigned.
• Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes
  作者：Spencer D. Dreher、Kamil Paruch、Thomas J. Katz

  DOI：10.1021/jo9914972

  日期：2000.2.1

  Alcohols containing HCl transform the hydroquinone reduction-products of helicenebisquinones into p-alkoxyphenols that have the alkoxyls specifically on the peripheries of the helices. The reactions are quick, and the yields are high. Alkoxyls at the 6-position are replaced also, but only after 2 h at 60 degrees C, not after the 5 min at 25 degrees C sufficient to replace the peripheral hydroxyls of the hydroquinones. After the remaining inside hydroxyls of a dihydroxytetramethoxy[6]helicene prepared by this procedure have been converted into camphanates, one diastereomer crystallizes from solution, allowing an enantiomer resolution to be carried out on a large scale. By then simply reapplying the procedure with alcoholic acid, a variety of resolved dihydroxytetraalkoxy[6]helicenes can be prepared in excellent yields without resolution procedures having to be developed for each, Similar procedures are effective when applied to a [7]carbohelicene.