1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone | 1374004-99-5

• 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)-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone
• 英文别名: 1-[3-(2-hydroxyacetyl)-5-phenylmethoxy-1H-indol-4-yl]-2-(3-methoxy-4-phenylmethoxyphenyl)ethanone
• CAS: 1374004-99-5
• 化学式: C₃₃H₂₉NO₆
• 分子量: 535.596
• InChiKey: SNHANIVNERAWDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[5-benzyloxy-3-(2-hydroxy-acetyl)-1H-indol-4-yl]-2-(4-benzyloxy-3-methoxy-phenyl)-ethanone 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-[5-benzyloxy-4-[2-(4-benzyloxy-3-methoxy-phenyl)-acetyl]-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-oxo-ethyl acetate
  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 甲醇 、 三正丁基氢锡 、 potassium carbonate 、 丙酸 、 potassium hydroxide 、 苯硼酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.0h， 生成 1-[5-benzyloxy-3-(2-hydroxy-acetyl)-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.