3,7-Dihydropyrano[3,2-e]indole-1-carbaldehyde | 1269985-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3,7-Dihydropyrano[3,2-e]indole-1-carbaldehyde
• CAS: 1269985-71-8
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: ZCGGZLWYPDILTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-羟基吲哚 在 caesium carbonate 、 三氯氧磷 作用下， 以 溴苯 、 丙酮 为溶剂， 生成 3,7-Dihydropyrano[3,2-e]indole-1-carbaldehyde
  参考文献：
  名称：

  Synthesis of dihydropyrano[3,2-e]indoles as rotationally restricted phenolic analogs of 5-hydroxyindole—thermal Claisen approach versus gold catalysis

  摘要：

  The Claisen rearrangement/cyclization of 5-propargyloxyindoles (2) to afford dihydropyrano[3,2-e]indoles (3) as direct precursors to tetrahydropyrano[3,2-e]indoles (1, a rotationally restricted phenolic analog of 5-hydroxyindole) was examined using either refluxing bromobenzene (156 degrees C) or Au(+1) catalysis in refluxing dioxane (101 degrees C). This transformation was best effected using Au(+1) catalysis (i.e., tris[triphenylphosphinegold(I)] oxonium tetrafluoroborate) because this method required a lower reaction temperature and gave better yields when compared to the simple thermal reaction conditions (156 C). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.084