6-benzyloxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester | 96277-44-0

• 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: 6-benzyloxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-6-phenylmethoxy-1H-indole-2-carboxylate
• CAS: 96277-44-0
• 化学式: C₂₈H₂₄N₂O₅
• 分子量: 468.509
• InChiKey: IEESHSDYPZGDOA-UHFFFAOYSA-N

物化性质

• 熔点：
  199-201 °C
• 沸点：
  692.1±55.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.75h， 以99%的产率得到6-benzyloxy-3-[2-(2-carboxybenzoylamino)ethyl]indole-2-carboxylic acid
  参考文献：
  名称：

  Nitrogen-containing compounds from the moss Fontinalis squamosa

  摘要：

  The alkaloid harmol and its hitherto unknown propionic acid derivative as well as a new amino acid derivative fontinalin were isolated from the watermoss Fontinalis squamosa. The structures have been elucidated spectroscopically and by independent chemical synthesis. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0031-9422(97)01034-0
• 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 6-benzyloxy-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