(1R,3R,5R,6R,9R,10R,13S,16R)-5,9,13-trimethyl-3-(trifluoromethyl)-2,4,14,15,17-pentaoxapentacyclo[11.3.1.0.^3,50.^6,160^10,16]heptadecane | 405261-74-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3R,5R,6R,9R,10R,13S,16R)-5,9,13-trimethyl-3-(trifluoromethyl)-2,4,14,15,17-pentaoxapentacyclo[11.3.1.0.^3,50.^6,160^10,16]heptadecane
• 英文别名: (1R,3R,5R,6S,9R,10S,13R,16R)-5,9,13-trimethyl-3-(trifluoromethyl)-2,4,14,15,17-pentaoxapentacyclo[11.3.1.03,5.06,16.010,16]heptadecane
• CAS: 405261-74-7
• 化学式: C₁₆H₂₁F₃O₅
• 分子量: 350.335
• InChiKey: BVGQGFWOTFOTCN-FKTNEPFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,3R,5R,6R,9R,10R,13S,16R)-5,9,13-trimethyl-3-(trifluoromethyl)-2,4,14,15,17-pentaoxapentacyclo[11.3.1.0.^3,50.^6,160^10,16]heptadecane 在 六氟异丙醇 作用下， 反应 1.0h， 以72%的产率得到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
• 作为产物：
  描述：

  青蒿素 在 吡啶 、 氯化亚砜 、 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 29.0h， 生成 (1R,3R,5R,6R,9R,10R,13S,16R)-5,9,13-trimethyl-3-(trifluoromethyl)-2,4,14,15,17-pentaoxapentacyclo[11.3.1.0.^3,50.^6,160^10,16]heptadecane
  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.