4,6,7-Trimethoxy-3-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>-1-(p-toluenesulfonyl)indole | 161156-08-7

• 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: 4,6,7-Trimethoxy-3-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>-1-(p-toluenesulfonyl)indole
• 英文别名: 2-trimethylsilylethyl N-[2-[4,6,7-trimethoxy-1-(4-methylphenyl)sulfonylindol-3-yl]ethyl]carbamate
• CAS: 161156-08-7
• 化学式: C₂₆H₃₆N₂O₇SSi
• 分子量: 548.733
• InChiKey: ZMJKSVBTVLROJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6,7-Trimethoxy-3-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>-1-(p-toluenesulfonyl)indole 在 ammonium cerium(IV) nitrate 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以78%的产率得到6-methoxy-3-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>-1-(tolylsulfonyl)indole-4,7-dione
  参考文献：
  名称：

  Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach

  摘要：

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).

  DOI：

  10.1021/jo00111a043
• 作为产物：
  描述：

  对硝基苯基三甲基硅乙基碳酸酯 、 1-(p-Toluenesulfonyl)-4,6,7-trimethoxytryptamine 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 4,6,7-Trimethoxy-3-<2-<<<2-(trimethylsilyl)ethoxy>carbonyl>amino>ethyl>-1-(p-toluenesulfonyl)indole
  参考文献：
  名称：

  Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach

  摘要：

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).

  DOI：

  10.1021/jo00111a043

文献信息

• Efficient Syntheses of the Marine Alkaloids Makaluvamine D and Discorhabdin C: The 4,6,7-Trimethoxyindole Approach
  作者：Eyyani V. Sadanandan、Sasi K. Pillai、M. V. Lakshmikantham、Adil D. Billimoria、J. Shane Culpepper、Michael P. Cava

  DOI：10.1021/jo00111a043

  日期：1995.3

  A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimine 23 is the late stage key intermediate in several previously reported syntheses of the biologically active pyrrolo[4,3,2-de]-quinoline marine alkaloids discorhabdin C (1) and makaluvamine D (3).