6-methyl-6-phenylspiro[1,2,4-trioxane-3,2'-adamantane] | 1188302-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧烷
• 英文名称: 6-methyl-6-phenylspiro[1,2,4-trioxane-3,2'-adamantane]
• CAS: 1188302-71-7
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: ASBDYEOGWFIVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  金刚烷酮 、 2,2,5,8,8-pentamethyl-5-phenyl-3,4,7-trioxa-2,8-disilanonane 在 CSA 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到6-methyl-6-phenylspiro[1,2,4-trioxane-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.