ethyl (2Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[2-(4-nitrophenyl)hydrazinylidene]pentanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl (2Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[2-(4-nitrophenyl)hydrazinylidene]pentanoate
• 英文别名: ethyl (2Z)-5-(1,3-dioxoisoindol-2-yl)-2-[(4-nitrophenyl)hydrazinylidene]pentanoate
• 化学式: C₂₁H₂₀N₄O₆
• 分子量: 424.413
• InChiKey: BPEIMULDZQFYJN-NKFKGCMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[2-(4-nitrophenyl)hydrazinylidene]pentanoate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到5-nitro-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  PTC‐Promoted Japp–Klingmann Reaction for the Synthesis of Indole Derivatives

  摘要：

  Indole derivatives have been efficiently synthesized from ethyl 2-phenylhydrazono-5-phthalimido-pentanoate and its derivatives, which were obtained by Japp-Klingmann reaction under phase-transfer catalytic (PTC) conditions. Several different phase-transfer catalysts were investigated and dimethyldioctadecyl ammonium chloride (DMDOA) was found to promote this reaction efficiently. Using DMDOA as the PTC, aryl hydrazones were obtained in yields of 90%. The pure aryl hydrazones were then efficiently cyclized to indole derivatives in yields of more than 80%.

  DOI：

  10.1081/scc-200057274
• 作为产物：
  描述：

  2-(3-N-邻苯二甲酰亚胺丙基)乙酰乙酸乙酯 、 4-硝基苯胺 在 盐酸 、 sodium nitrite 、 双十八烷基二甲基氯化铵 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 以99%的产率得到ethyl (2Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[2-(4-nitrophenyl)hydrazinylidene]pentanoate
  参考文献：
  名称：

  PTC‐Promoted Japp–Klingmann Reaction for the Synthesis of Indole Derivatives

  摘要：

  Indole derivatives have been efficiently synthesized from ethyl 2-phenylhydrazono-5-phthalimido-pentanoate and its derivatives, which were obtained by Japp-Klingmann reaction under phase-transfer catalytic (PTC) conditions. Several different phase-transfer catalysts were investigated and dimethyldioctadecyl ammonium chloride (DMDOA) was found to promote this reaction efficiently. Using DMDOA as the PTC, aryl hydrazones were obtained in yields of 90%. The pure aryl hydrazones were then efficiently cyclized to indole derivatives in yields of more than 80%.

  DOI：

  10.1081/scc-200057274