ethyl 3-(2-phthalimidoethyl) indole-2-carboxylate | 55747-55-2

• 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: ethyl 3-(2-phthalimidoethyl) indole-2-carboxylate
• 英文别名: ethyl 3-[2-(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)ethyl]-1H-2-indolecarboxylate；3-(2-phthalimido-ethyl)-indole-2-carboxylic acid ethyl ester；3-(2-Phthalimido-aethyl)-indol-2-carbonsaeure-aethylester；ethyl 3-[2-(1,3-dioxoisoindol-2-yl)ethyl]-1H-indole-2-carboxylate
• CAS: 55747-55-2
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: FWOFFJLECPSDJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 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：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-phthalimidoethyl) indole-2-carboxylate 在 一水合肼 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以52%的产率得到2,3,4,9-tetrahydro-1H-β-carbolin-1-one
  参考文献：
  名称：

  Lingam; Muralimohan Rao; Bhowmik, Dipal R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 12, p. 2049 - 2052

  摘要：

  DOI：
• 作为产物：
  描述：

  2-phenylhydrazono-5-phthalimido-pentanoic acid ethyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到ethyl 3-(2-phthalimidoethyl) indole-2-carboxylate
  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

• Keimatsu; Sugasawa; Kasuya, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, # 8, p. 107
  作者：Keimatsu、Sugasawa、Kasuya

  DOI：——

  日期：——
• 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%.
• Lingam; Muralimohan Rao; Bhowmik, Dipal R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 12, p. 2049 - 2052
  作者：Lingam、Muralimohan Rao、Bhowmik, Dipal R.、Islam, Aminul

  DOI：——

  日期：——