3,7-Dihydropyrano[3,2-e]indole | 1269985-75-2

• 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
• CAS: 1269985-75-2
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: DFXWUIHHCSDCHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-propargyloxyindole 在 tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 以50%的产率得到3,7-Dihydropyrano[3,2-e]indole
  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

文献信息

• Synthesis of dihydropyrano[3,2-e]indoles as rotationally restricted phenolic analogs of 5-hydroxyindole—thermal Claisen approach versus gold catalysis
  作者：George N. Karageorge、John E. Macor

  DOI：10.1016/j.tetlet.2010.12.084

  日期：2011.3

  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.