7-[(4-Chlorophenyl)sulfanylmethyl]-7-methylspiro[1,2,4-trioxepane-3,2'-adamantane] | 869661-33-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 7-[(4-Chlorophenyl)sulfanylmethyl]-7-methylspiro[1,2,4-trioxepane-3,2'-adamantane]
• CAS: 869661-33-6
• 化学式: C₂₁H₂₇ClO₃S
• 分子量: 394.963
• InChiKey: BLVIYSFJSDYNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-[(4-Chlorophenyl)sulfanylmethyl]-7-methylspiro[1,2,4-trioxepane-3,2'-adamantane] 在 2,6-二甲基吡啶 、 sodium hydroxide 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of 1,2,4-trioxepanes via application of thiol-olefin Co-oxygenation methodology

  摘要：

  Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates beta-hydroxy peroxides that can be condensed in situ with various ketones, to afford a series of functionalised 1,2,4-trioxepanes in good yields. Manipulation of the phenylsulfenyl group in 8a-8c allows for convenient modification to the spiro-trioxepane substituents. Surprisingly, and in contrast to the 1,2,4-trioxanes examined, 1,2,4-trioxepanes are inactive as antimalarials up to 1000 nM and we rationalize this observation based on the inherent stability of these systems to ferrous mediated degradation. FMO calculations clearly show that the sigma* orbital of the peroxide moiety of 1,2,4-trioxane derivatives 4a and 14b are lower in energy and more accessible to attack by Fe(II) compared to their trioxepane analogues 8b and 9b.

  DOI：

  10.1016/j.bmcl.2006.08.098
• 作为产物：
  描述：

  4-(4'-chlorophenyl)-3-hydroperoxy-3-methylbutanol 、 金刚烷酮 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以80%的产率得到7-[(4-Chlorophenyl)sulfanylmethyl]-7-methylspiro[1,2,4-trioxepane-3,2'-adamantane]
  参考文献：
  名称：

  Synthesis of 1,2,4-trioxepanes via application of thiol-olefin Co-oxygenation methodology

  摘要：

  Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates beta-hydroxy peroxides that can be condensed in situ with various ketones, to afford a series of functionalised 1,2,4-trioxepanes in good yields. Manipulation of the phenylsulfenyl group in 8a-8c allows for convenient modification to the spiro-trioxepane substituents. Surprisingly, and in contrast to the 1,2,4-trioxanes examined, 1,2,4-trioxepanes are inactive as antimalarials up to 1000 nM and we rationalize this observation based on the inherent stability of these systems to ferrous mediated degradation. FMO calculations clearly show that the sigma* orbital of the peroxide moiety of 1,2,4-trioxane derivatives 4a and 14b are lower in energy and more accessible to attack by Fe(II) compared to their trioxepane analogues 8b and 9b.

  DOI：

  10.1016/j.bmcl.2006.08.098