5-hydroperoxy-4-methylene-1-phenyl-hexane-1,6-diol | 627077-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-hydroperoxy-4-methylene-1-phenyl-hexane-1,6-diol
• 英文别名: 5-Hydroperoxy-4-methylidene-1-phenylhexane-1,6-diol
• CAS: 627077-78-5
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: LUPSUZWVPGYXKD-UHFFFAOYSA-N

物化性质

• 沸点：
  459.6±45.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroperoxy-4-methylene-1-phenyl-hexane-1,6-diol 在 chromium trioxide pyridine 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-phenyl-4-(1,2,5-trioxaspiro[5.5]undecan-3-yl)pent-4-en-1-one
  参考文献：
  名称：

  Synthesis of new 6-alkylvinyl/arylalkylvinyl substituted 1,2,4-trioxanes active against multidrug-resistant malaria in mice

  摘要：

  3-Alkyl/arylalkyl substituted 2-butenols 9, 10, 23a-d undergo regiospecific photooxygenation to furnish beta-hydroxyhydroperoxides 11, 12, 24-a-d, respectively, in reasonable yields. Acid catalyzed condensation of 11, 12, 24a-d with various ketones furnish new 1,2,4-trioxanes 13-18, 25a-d, 26a-d, 27a-d in good yields. Several of these trioxanes show promising antimalarial activity against multidrug-resistant Plasmodium yoelii in mice by oral and intramuscular routes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.005
• 作为产物：
  描述：

  (E)-6-acetoxy-4-methyl-4-hexenal 在 氧气 、 亚甲兰 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 9.0h， 生成 5-hydroperoxy-4-methylene-1-phenyl-hexane-1,6-diol
  参考文献：
  名称：

  Synthesis of new 6-alkylvinyl/arylalkylvinyl substituted 1,2,4-trioxanes active against multidrug-resistant malaria in mice

  摘要：

  3-Alkyl/arylalkyl substituted 2-butenols 9, 10, 23a-d undergo regiospecific photooxygenation to furnish beta-hydroxyhydroperoxides 11, 12, 24-a-d, respectively, in reasonable yields. Acid catalyzed condensation of 11, 12, 24a-d with various ketones furnish new 1,2,4-trioxanes 13-18, 25a-d, 26a-d, 27a-d in good yields. Several of these trioxanes show promising antimalarial activity against multidrug-resistant Plasmodium yoelii in mice by oral and intramuscular routes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.005

文献信息

• Geraniol-derived 1,2,4-Trioxanes with potent in-vivo antimalarial activity
  作者：Chandan Singh、Nitin Gupta、Sunil K Puri

  DOI：10.1016/s0960-894x(03)00782-0

  日期：2003.10

  Geraniol, an abundantly available naturally occurring allylic alcohol, has been used as a starting material to prepare a series of 6-[alpha-(3'-aryl-3-hydroxypropyl)vinyl]-1,2,4-trioxanes. Some of these novel trioxanes have shown very promising antimalarial activity against multi-drug resistant Plasmodium yoelii in mice by both intramuscular (im) and oral routes. (C) 2003 Elsevier Ltd. All rights reserved.