6,11-Bis[tri(propan-2-yl)silyloxy]hexahelicene-1,4,13,16-tetrone | 261776-68-5

• 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: 6,11-Bis[tri(propan-2-yl)silyloxy]hexahelicene-1,4,13,16-tetrone
• CAS: 261776-68-5
• 化学式: C₄₄H₅₂O₆Si₂
• 分子量: 733.064
• InChiKey: RAVCJNRAIJXJLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.88
• 重原子数：
  52
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,11-Bis[tri(propan-2-yl)silyloxy]hexahelicene-1,4,13,16-tetrone 在 sodium dithionite 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2,7-Bis-triisopropylsilanyloxy-phenanthro[3,4-c]phenanthrene-9,12,13,16-tetraol
  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：

  2,7-diacetylnaphthalene 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 73.0h， 生成 6,11-Bis[tri(propan-2-yl)silyloxy]hexahelicene-1,4,13,16-tetrone
  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

文献信息

• 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.