1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1-benzyl-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone | 1374004-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1-benzyl-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone
• 英文别名: 1-[1-Benzyl-3-(2-hydroxyacetyl)-5-phenylmethoxyindol-4-yl]-2-(3-methoxy-4-phenylmethoxyphenyl)ethanone；1-[1-benzyl-3-(2-hydroxyacetyl)-5-phenylmethoxyindol-4-yl]-2-(3-methoxy-4-phenylmethoxyphenyl)ethanone
• CAS: 1374004-84-8
• 化学式: C₄₀H₃₅NO₆
• 分子量: 625.721
• InChiKey: CBHYOAHBTYWWPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1-benzyl-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone 在 potassium tert-butylate 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以24%的产率得到1-benzyl-6-benzyloxy-5-(4-benzyloxy-3-methoxy-benzyl)-4-hydroxy-1H-benzo[cd]indol-3-one
  参考文献：
  名称：

  Synthetic studies of decursivine derivatives: preparation of key indole alkaloids via α-hydroxyalkylation

  摘要：

  2-Hydroxyacetyl indole modified at C-3 position was prepared with an eye to developing a total synthesis of decursivine derivatives (decursivine, serotobenine, moschaminindolol, and flavumindole). The indole was prepared through a sequence of oxalyl chloride introduction at C-3 position of indole and acid chloride reduction with tributyltin hydride. In addition, we report a novel synthesis of fully functionalized Uhle's ketone via ortho-selective alpha-hydroxyallcylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.026
• 作为产物：
  描述：

  [4-(苄氧基)-3-甲氧基苯基]乙醛 在 吡啶 、 甲醇 、 双氧水 、 三正丁基氢锡 、 potassium carbonate 、 丙酸 、 三乙胺 、 potassium hydroxide 、 苯硼酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 41.5h， 生成 1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1-benzyl-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone
  参考文献：
  名称：

  Synthetic studies of decursivine derivatives: preparation of key indole alkaloids via α-hydroxyalkylation

  摘要：

  2-Hydroxyacetyl indole modified at C-3 position was prepared with an eye to developing a total synthesis of decursivine derivatives (decursivine, serotobenine, moschaminindolol, and flavumindole). The indole was prepared through a sequence of oxalyl chloride introduction at C-3 position of indole and acid chloride reduction with tributyltin hydride. In addition, we report a novel synthesis of fully functionalized Uhle's ketone via ortho-selective alpha-hydroxyallcylation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.026

文献信息

• Synthetic studies of decursivine derivatives: preparation of key indole alkaloids via α-hydroxyalkylation
  作者：Fumihiro Ito、Kentaro Yamaguchi

  DOI：10.1016/j.tet.2012.03.026

  日期：2012.5

  2-Hydroxyacetyl indole modified at C-3 position was prepared with an eye to developing a total synthesis of decursivine derivatives (decursivine, serotobenine, moschaminindolol, and flavumindole). The indole was prepared through a sequence of oxalyl chloride introduction at C-3 position of indole and acid chloride reduction with tributyltin hydride. In addition, we report a novel synthesis of fully functionalized Uhle's ketone via ortho-selective alpha-hydroxyallcylation. (C) 2012 Elsevier Ltd. All rights reserved.