2,2,2-trifluoro-1-[(1S,4R,5S,8R,9R,11R,12S)-1,5,9-trimethyl-10,13,14,15-tetraoxatetracyclo[9.3.1.0.^4,120^8,12]pentadec-9-yl]-1-ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2,2,2-trifluoro-1-[(1S,4R,5S,8R,9R,11R,12S)-1,5,9-trimethyl-10,13,14,15-tetraoxatetracyclo[9.3.1.0.^4,120^8,12]pentadec-9-yl]-1-ethanone
• 英文别名: 2,2,2-trifluoro-1-[(1R,4S,5R,8S,9R,11R,12R)-1,5,9-trimethyl-10,13,14,15-tetraoxatetracyclo[9.3.1.04,12.08,12]pentadecan-9-yl]ethanone
• 化学式: C₁₆H₂₁F₃O₅
• 分子量: 350.335
• InChiKey: LSTGGLUODLSLBQ-XMNQTZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  青蒿素 在 吡啶 、 氯化亚砜 、 六氟异丙醇 、 四丁基氟化铵 、 水 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 2,2,2-trifluoro-1-[(1S,4R,5S,8R,9R,11R,12S)-1,5,9-trimethyl-10,13,14,15-tetraoxatetracyclo[9.3.1.0.^4,120^8,12]pentadec-9-yl]-1-ethanone
  参考文献：
  名称：

  Anhydrodihydroartemisinin and Its 10-Trifluoromethyl Analogue:  Access to Novel D-Ring-Contracted Artemisinin Trifluoromethyl Ketones

  摘要：

  The preparation of the 10-trifluoromethyl hydroartemisinin, followed by dehydration, afforded the trifluoromethyl analogue 2 of anhydrodihydroartemisinin 1. The reactivity of these two glycals of artemisinin were compared in epoxidation and halogenation reactions. Iodination of glycal 1 in water and the further rearrangement of the produced iodo hemiacetal provided the new D-ring-contracted aldehyde 8alpha, where the methyl at C-9 is beta. Epoxidation of 10-trifluoromethyl anhydrodihydroartemisinin 2 stereoselectively provided the beta-epoxy ether 11 in high yield. When treated with hexafluoro-2-propanol or trifluoroethanol, 11 readily underwent a rearrangement yielding to the D-ring-contracted trifluoromethyl ketone 9alpha with retention of configuration at C-9.

  DOI：

  10.1021/jo016091f

文献信息

• Anhydrodihydroartemisinin and Its 10-Trifluoromethyl Analogue:  Access to Novel D-Ring-Contracted Artemisinin Trifluoromethyl Ketones
  作者：Fabienne Grellepois、Fatima Chorki、Benoit Crousse、Michèle Ourévitch、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1021/jo016091f

  日期：2002.2.1

  The preparation of the 10-trifluoromethyl hydroartemisinin, followed by dehydration, afforded the trifluoromethyl analogue 2 of anhydrodihydroartemisinin 1. The reactivity of these two glycals of artemisinin were compared in epoxidation and halogenation reactions. Iodination of glycal 1 in water and the further rearrangement of the produced iodo hemiacetal provided the new D-ring-contracted aldehyde 8alpha, where the methyl at C-9 is beta. Epoxidation of 10-trifluoromethyl anhydrodihydroartemisinin 2 stereoselectively provided the beta-epoxy ether 11 in high yield. When treated with hexafluoro-2-propanol or trifluoroethanol, 11 readily underwent a rearrangement yielding to the D-ring-contracted trifluoromethyl ketone 9alpha with retention of configuration at C-9.