5-nitro-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester | 55747-58-5

• 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: 5-nitro-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-YL)ethyl]-5-nitro-1H-indole-2-carboxylate；ethyl 3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-5-nitro-1H-indole-2-carboxylate
• CAS: 55747-58-5
• 化学式: C₂₁H₁₇N₃O₆
• mdl: MFCD00227129
• 分子量: 407.382
• InChiKey: VFHDPCNWQXZWQU-UHFFFAOYSA-N

物化性质

• 沸点：
  656.9±55.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(3-N-邻苯二甲酰亚胺丙基)乙酰乙酸乙酯 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 9.5h， 生成 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

文献信息

• PTC‐Promoted Japp–Klingmann Reaction for the Synthesis of Indole Derivatives
  作者：Wei He、Bang‐Le Zhang、Zhong‐Jie Li、Sheng‐Yong Zhang

  DOI：10.1081/scc-200057274

  日期：2005.5.1

  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%.