6α-hydroxy-7α-hydroxymethyl-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole | 142502-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6α-hydroxy-7α-hydroxymethyl-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole
• CAS: 142502-26-9
• 化学式: C₂₄H₂₇NO₄S
• 分子量: 425.549
• InChiKey: NIIVQVFGMSJDSL-BAMASNGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.53
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6α-hydroxy-7α-hydroxymethyl-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole 在 4-二甲氨基吡啶 、 sodium hydroxide 、 四丁基硫酸氢铵 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.5h， 生成 6α-benzoyloxy-7α-benzyloxymethyl-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole
  参考文献：
  名称：

  Structure-function relationship of Yuehchukene II. The effect of C-6 indole rotation on anti-implantation activity

  摘要：

  In a first attempts to define the structural requirements for the expression of anti-implantation activity in Yuehchukene (YCK), it was found that the relative position or planarity of the aromatic centres may be crucial. New synthetic routes leading to analogues with modification of C-7 substituents were established. Results indicated that a bulky group at C-7 that served to restrict the rotation of the C-6 indole was indispensable. Further steric hindrance by 2'-methyl would increase potency in all weak analogues. It was concluded that YCK required an optimal conformation that was defined by a narrowly-fixed angle between the, planes of the C-6 indole and the tetracyclic unit.

  DOI：

  10.1016/0223-5234(92)90100-f
• 作为产物：
  描述：

  7α-methoxycarbonyl-9α-methyl-6-oxo-5,6,6aβ,7β,8,9aβ,10,10β-octahydroindeno<2,1-b>indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以36%的产率得到6α-hydroxy-7α-hydroxymethyl-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole
  参考文献：
  名称：

  Structure-function relationship of Yuehchukene II. The effect of C-6 indole rotation on anti-implantation activity

  摘要：

  In a first attempts to define the structural requirements for the expression of anti-implantation activity in Yuehchukene (YCK), it was found that the relative position or planarity of the aromatic centres may be crucial. New synthetic routes leading to analogues with modification of C-7 substituents were established. Results indicated that a bulky group at C-7 that served to restrict the rotation of the C-6 indole was indispensable. Further steric hindrance by 2'-methyl would increase potency in all weak analogues. It was concluded that YCK required an optimal conformation that was defined by a narrowly-fixed angle between the, planes of the C-6 indole and the tetracyclic unit.

  DOI：

  10.1016/0223-5234(92)90100-f