1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-dimethoxy[6]helicene | 142743-48-4

• 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: 1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-dimethoxy[6]helicene
• 英文别名: 6,11-dimethoxyhexahelicene-1,4,13,16-tetrone
• CAS: 142743-48-4
• 化学式: C₂₈H₁₆O₆
• 分子量: 448.431
• InChiKey: FSHYPNOPQAGCJL-UHFFFAOYSA-N

物化性质

• 沸点：
  795.4±60.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-dimethoxy[6]helicene 在 盐酸 、 sodium dithionite 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 2,7,9,16-tetraethoxy-phenanthro[3,4-c]phenanthrene-12,13-diol
  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 吡啶 、 三甲基氯硅烷 、 对甲苯磺酸 、 苯甲酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 70.0h， 生成 1,4,13,16-tetrahydro-1,4,13,16-tetraoxo-6,11-dimethoxy[6]helicene
  参考文献：
  名称：

  功能化螺旋的有效合成

  摘要：

  [5]-和[6]螺旋烯双醌可以通过将1,4-二乙酰苯或2,7-二乙酰萘的烯醇醚与对苯醌组合而容易且大量制备。类似的二乙烯基芳烃要么没有醚官能团，要么没有连接到双键上，而是连接到芳环上，只能以低产率和低纯度得到相应的螺旋。[6] Helicenebisquinone 11c 被拆分成它的对映异构体。这些对映异构体之一和 l-脯氨醇的加合物的 X 射线衍射分析显示了 11c 的绝对立体化学和胺与醌加成的区域化学。

  DOI：

  10.1021/ja9721327

文献信息

• Willmore, Nikolaos D.; Liu, Longbin; Katz, Thomas J., Angewandte Chemie, 1992, vol. 104, # 8, p. 1081 - 1082
  作者：Willmore, Nikolaos D.、Liu, Longbin、Katz, Thomas J.

  DOI：——

  日期：——
• 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.
• An Efficient Synthesis of Functionalized Helicenes
  作者：Thomas J. Katz、Longbin Liu、Nikolaos D. Willmore、Joseph M. Fox、Arnold L. Rheingold、Shuhao Shi、Colin Nuckolls、Barry H. Rickman

  DOI：10.1021/ja9721327

  日期：1997.10.1

  aromatic rings, give the corresponding helicenes in only low yields and low purities. [6]Helicenebisquinone 11c is resolved into its enantiomers. An X-ray diffraction analysis of the adduct of one of these enantiomers and l-prolinol shows the absolute stereochemistry of 11c and the regiochemistry with which the amine adds to the quinone.

  [5]-和[6]螺旋烯双醌可以通过将1,4-二乙酰苯或2,7-二乙酰萘的烯醇醚与对苯醌组合而容易且大量制备。类似的二乙烯基芳烃要么没有醚官能团，要么没有连接到双键上，而是连接到芳环上，只能以低产率和低纯度得到相应的螺旋。[6] Helicenebisquinone 11c 被拆分成它的对映异构体。这些对映异构体之一和 l-脯氨醇的加合物的 X 射线衍射分析显示了 11c 的绝对立体化学和胺与醌加成的区域化学。