N-(2,2-dimethoxyethyl)-5-methoxy-1H-indole-2-carboxamide

• 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: N-(2,2-dimethoxyethyl)-5-methoxy-1H-indole-2-carboxamide
• 英文别名: 5-methoxy-indole-2-carboxylic acid-(2,2-dimethoxy-ethylamide)；5-Methoxy-indol-2-carbonsaeure-(2,2-dimethoxy-aethylamid)；N-(2,2-Dimethoxyethyl)-5-methoxyindole-2-carboxamide
• 化学式: C₁₄H₁₈N₂O₄
• 分子量: 278.308
• InChiKey: QNSNPRYFKPPXFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-5-methoxy-1H-indole-2-carboxamide 在 polyphosphoric acid(PPA) 作用下， 反应 0.5h， 以88%的产率得到6-methoxy-2,9-dihydro-1H-pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones

  摘要：

  A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 degrees C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus.

  DOI：

  10.1055/s-0033-1339155
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 、 乙酰氯 作用下， 生成 N-(2,2-dimethoxyethyl)-5-methoxy-1H-indole-2-carboxamide
  参考文献：
  名称：

  Blaikie; Perkin, Journal of the Chemical Society, 1924, vol. 125, p. 313

  摘要：

  DOI：

文献信息

• Blaikie; Perkin, Journal of the Chemical Society, 1924, vol. 125, p. 313
  作者：Blaikie、Perkin

  DOI：——

  日期：——
• A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones
  作者：Giuseppe La Regina、Valeria Famiglini、Sara Passacantilli、Sveva Pelliccia、Pasqualina Punzi、Romano Silvestri

  DOI：10.1055/s-0033-1339155

  日期：——

  A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 degrees C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus.