5-Methyl-5-phenylspiro[1,2,4-trioxolane-3,2'-adamantane] | 869672-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: 5-Methyl-5-phenylspiro[1,2,4-trioxolane-3,2'-adamantane]
• CAS: 869672-26-4
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: KRZKVNBLQDLYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酮 、 adamantan-2-one O-methyloxime 在 臭氧 作用下， 以37%的产率得到5-Methyl-5-phenylspiro[1,2,4-trioxolane-3,2'-adamantane]
  参考文献：
  名称：

  Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs: Relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity

  摘要：

  These data suggest that iron(II) reactivity for a set of homologous spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane peroxide heterocycles is a necessary, but insufficient, property of animalarial peroxides. Heme alkylation efficiency appears to give a more accurate prediction of antimalarial activity than FeSO4-mediated reaction rates, suggesting that antimalarial activity is not merely dependent on peroxide bond cleavage, but also on the ability of reactive intermediates to alkylate heme or other proximal targets. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.013

文献信息

• Spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane pairs: Relationship between peroxide bond iron(II) reactivity, heme alkylation efficiency, and antimalarial activity
  作者：Xiaofang Wang、Darren J. Creek、Charles E. Schiaffo、Yuxiang Dong、Jacques Chollet、Christian Scheurer、Sergio Wittlin、Susan A. Charman、Patrick H. Dussault、James K. Wood、Jonathan L. Vennerstrom

  DOI：10.1016/j.bmcl.2009.07.013

  日期：2009.8

  These data suggest that iron(II) reactivity for a set of homologous spiroadamantyl 1,2,4-trioxolane, 1,2,4-trioxane, and 1,2,4-trioxepane peroxide heterocycles is a necessary, but insufficient, property of animalarial peroxides. Heme alkylation efficiency appears to give a more accurate prediction of antimalarial activity than FeSO4-mediated reaction rates, suggesting that antimalarial activity is not merely dependent on peroxide bond cleavage, but also on the ability of reactive intermediates to alkylate heme or other proximal targets. (C) 2009 Elsevier Ltd. All rights reserved.