4-(hydroxyethyl)-3-(prop-1-en-2-yl)-spiro[1,2,4-trioxacyclohexane-3,2'-adamantane]

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(hydroxyethyl)-3-(prop-1-en-2-yl)-spiro[1,2,4-trioxacyclohexane-3,2'-adamantane]
• 英文别名: 2-(6-prop-1-en-2-ylspiro[1,2,4-trioxane-3,2'-adamantane]-5-yl)ethanol
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: YSGUXVWBUBKATK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(hydroxyethyl)-3-(prop-1-en-2-yl)-spiro[1,2,4-trioxacyclohexane-3,2'-adamantane] 、 青蒿琥酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以26%的产率得到1-O-[2-(6-prop-1-en-2-ylspiro[1,2,4-trioxane-3,2'-adamantane]-5-yl)ethyl] 4-O-[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] butanedioate
  参考文献：
  名称：

  Antimalarial Peroxide Dyads from Natural Artemisinin and Hydroxyalkylated 1,2,4-Trioxanes

  摘要：

  Three synthetic approaches to highly antimalarial peroxide dyads that are composed of the natural artemisinin part (either as dihydroartemisinin or artesunic acid components) and synthetic 1,2,4-trioxanes linked by ether or ester bridges are described. Photooxygenation is the key step to introduce the trioxane group initially or at the end of the reaction sequence, respectively. Dihydroartemisinin or artesunate coupling to hydroxyethyltrioxanes are the two processes that use intact peroxide units from the beginning, whereas the dihydroartemisinin-coupling to an allylic alcohol is a postphotooxygenation route, where the second trioxane ring is installed in the last step of the procedure.

  DOI：

  10.1021/jm9002523