4-nitrobenzyl-[1-(2-methoxymethyl-allyl)-1H-indol-3-ylmethylene]-amine

• 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: 4-nitrobenzyl-[1-(2-methoxymethyl-allyl)-1H-indol-3-ylmethylene]-amine
• 英文别名: 1-[1-[2-(methoxymethyl)prop-2-enyl]indol-3-yl]-N-[(4-nitrophenyl)methyl]methanimine
• 化学式: C₂₁H₂₁N₃O₃
• 分子量: 363.416
• InChiKey: TVWWXGHKQQMJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基-2-氯甲基丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 4-nitrobenzyl-[1-(2-methoxymethyl-allyl)-1H-indol-3-ylmethylene]-amine
  参考文献：
  名称：

  Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation

  摘要：

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.

  DOI：

  10.1021/ol060485h

文献信息

• Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation
  作者：Rebecca M. Wilson、Reema K. Thalji、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ol060485h

  日期：2006.4.1

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.