3,5,6-tri(2-methylbut-3-yn-2-yloxy)-9-oxo-9H-xanthen-1-yl acetate | 1313722-42-7

• 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: 3,5,6-tri(2-methylbut-3-yn-2-yloxy)-9-oxo-9H-xanthen-1-yl acetate
• CAS: 1313722-42-7
• 化学式: C₃₀H₂₈O₇
• 分子量: 500.548
• InChiKey: TWOSEZGGEFCCLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.2
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,5,6-tri(2-methylbut-3-yn-2-yloxy)-9-oxo-9H-xanthen-1-yl acetate 在 盐酸 、 10 % Pd-BaSO4 、 水 、 氢气 、 ethylenediamine Tetraacetic Acid 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 gambogin
  参考文献：
  名称：

  Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

  摘要：

  The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.0(3,7)] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.029
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 17.5h， 生成 3,5,6-tri(2-methylbut-3-yn-2-yloxy)-9-oxo-9H-xanthen-1-yl acetate
  参考文献：
  名称：

  Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

  摘要：

  The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.0(3,7)] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.029