7α-benzyloxymethyl-6α-hydroxy-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole | 142502-27-0

• 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: 7α-benzyloxymethyl-6α-hydroxy-9α-methyl-5-tosyl-5,6β,6aβ,7β,8,9β,10,10aβ-octahydroindeno<2,1-b>indole
• CAS: 142502-27-0
• 化学式: C₃₁H₃₃NO₄S
• 分子量: 515.673
• InChiKey: IEHQRGLRGOKCIC-HSYDBHIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7α-benzyloxymethyl-6α-hydroxy-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 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.5h， 生成 7α-benzyloxymethyl-6β-indol-3'-yl-9α-methyl-5-tosyl-5,6α,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：

  在 PtO₂/C sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 苯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 4.5h， 生成 7α-benzyloxymethyl-6α-hydroxy-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