(M,M)-(-)-[5]HELOL | 261784-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (M,M)-(-)-[5]HELOL
• 英文别名: 5-(4-hydroxy-7,10-dimethoxy-5-pentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaenyl)-7,10-dimethoxypentacyclo[12.8.0.02,11.03,8.017,22]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaen-4-ol
• CAS: 261784-42-3
• 化学式: C₄₈H₃₄O₆
• 分子量: 706.794
• InChiKey: NPVHNPYBRHEFFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  54
• 可旋转键数：
  5
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (M,M)-(-)-[5]HELOL 在 4-二甲氨基吡啶 、 三乙胺 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  [5]HELOL Phosphite：一种远程手性螺旋槽传感器

  摘要：

  即使当第一个手性中心远离官能团时，如果官能团连接到嵌入非外消旋螺旋凹槽内的磷上，也可以感知手性分子的立体化学。使用的传感器是 [5] HELOL 的亚磷酸酯，结构 6，31P NMR 光谱是分析方法。尽管羟基和第一个手性中心之间有七个亚甲基，但 31P NMR 可以区分具有基线分辨率的 8-苯基壬醇的对映异构体。然而，为了达到这个分辨率，必须适当地选择溶剂。该探针还可以分析其他醇类、胺类、酚类的对映异构体，当它们与 2-氨基苯酚偶联时，还可以分析羧酸。

  DOI：

  10.1021/ja001904n
• 作为产物：
  描述：

  5,7-Dimethoxy-dibenzo[c,g]phenanthren-10-ol 在 三乙胺 、 silver(l) oxide 、 锌 作用下， 以 溶剂黄146 为溶剂， 生成 (M,M)-(-)-[5]HELOL
  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

• Application of the Russig−Laatsch Reaction to Synthesize a Bis[5]helicene Chiral Pocket for Asymmetric Catalysis
  作者：Spencer D. Dreher、Thomas J. Katz、Kin-Chung Lam、Arnold L. Rheingold

  DOI：10.1021/jo991498u

  日期：2000.2.1

  The enantiomers of a bis[5]helicenediol Ligand ([5]HELOL) have been synthesized in appreciable amounts by a procedure in which key steps are the union of p-benzoquinone with an enol ether of 3-acetylphenanthrene and the displacement of phenol and phenol ether functions by alcohols (the Russig-Laatsch reaction). This diol catalyzes the addition of diethylzinc to aldehydes and gives nonracemic alcohols with enantiomeric excesses as high as 81%. The stereoselectivities and yields are much greater than when the catalyzing diol is BINOL. The enantioselectivities are greater also than those of other reactions catalyzed by helicene ligands.