2,2-difluoro-1-(2,5-dimethoxyphenyl)-2-[(1S,4R,5S,8R,9R,10S,12R,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,13.0^8,13]hexadec-10-yl]-1-ethanone

• 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: 2,2-difluoro-1-(2,5-dimethoxyphenyl)-2-[(1S,4R,5S,8R,9R,10S,12R,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,13.0^8,13]hexadec-10-yl]-1-ethanone
• 英文别名: 1-(2,5-dimethoxyphenyl)-2,2-difluoro-2-[(1R,4S,5R,8S,9S,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]ethanone
• 化学式: C₂₅H₃₂F₂O₇
• 分子量: 482.522
• InChiKey: BJJWECYGSHWLOE-HIGCBAFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  dihydroartemisinin acetate 、 [1-(2,5-Dimethoxyphenyl)-2,2-difluoroethenoxy]-trimethylsilane 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-difluoro-1-(2,5-dimethoxyphenyl)-2-[(1S,4R,5S,8R,9R,10S,12R,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,13.0^8,13]hexadec-10-yl]-1-ethanone 、 2,2-difluoro-1-(2,5-dimethoxyphenyl)-2-[(1S,4R,5S,8R,9R,10R,12R,13S)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^4,13.0^8,13]hexadec-10-yl]-1-ethanone
  参考文献：
  名称：

  C-10-Fluorinated derivatives of dihydroartemisinin: difluoromethylene ketones

  摘要：

  Difluoroenoxysilanes, prepared from aromatic and heterocyclic ketones, reacted with dihydroartemisinin acetate in the presence of Lewis acid to provide in good to moderate yields the 10-substituted difluoromethylene ketones. The introduction of the difluoromethylketone moiety was accompanied by the epimerisation of C-9. Best results were obtained using SnCl4 as Lewis acid. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)02272-3

文献信息

• Fluoro Artemisinins: Difluoromethylene Ketones
  作者：Fatima Chorki、Fabienne Grellepois、Benoit Crousse、Michèle Ourévitch、Danièle Bonnet-Delpon、Jean-Pierre Bégué

  DOI：10.1021/jo0158579

  日期：2001.11.1

  corresponding difluoromethylene ketol adducts in good yields. Similar Lewis acid catalyzed reactions of dihydroartemisinin acetate with the difluoroenoxysilanes provided the 10-substituted difluoromethylene ketones in good to moderate yields. Interestingly enough, the course and the stereochemistry of these reactions are highly dependent on the nature of the Lewis acids used; the addition reaction was accompanied

  在 BF(3).Et(2)O 存在下，衍生自脱水二氢青蒿素的环缩醛与 gem-二氟烯氧基硅烷的反应以良好的产率提供了相应的二氟亚甲基酮醇加合物。类似的路易斯酸催化二氢青蒿素乙酸酯与二氟烯氧基硅烷的反应以良好至中等的产率提供了 10-取代的二氟亚甲基酮。有趣的是，这些反应的过程和立体化学高度依赖于所用路易斯酸的性质。加成反应伴随着 C-9 处的差向异构化，C-10 处的立体化学取决于所用的二氟烯氧基硅烷。最好的结果是使用 SnCl(4) 获得高立体选择性的 9alpha,10beta 立体异构体。当 0。
• C-10-Fluorinated derivatives of dihydroartemisinin: difluoromethylene ketones
  作者：Fatima Chorki、Benoı̂t Crousse、Danièle Bonnet-Delpon、Jean-Pierre Bégué、Thierry Brigaud、Charles Portella

  DOI：10.1016/s0040-4039(00)02272-3

  日期：2001.2

  Difluoroenoxysilanes, prepared from aromatic and heterocyclic ketones, reacted with dihydroartemisinin acetate in the presence of Lewis acid to provide in good to moderate yields the 10-substituted difluoromethylene ketones. The introduction of the difluoromethylketone moiety was accompanied by the epimerisation of C-9. Best results were obtained using SnCl4 as Lewis acid. (C) 2001 Published by Elsevier Science Ltd.