4,4-dihydroperoxyheptane

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 英文名称: 4,4-dihydroperoxyheptane
• 英文别名: 4,4‐dihydroperoxyheptane；4,4-Dihydroperoxyheptane
• 化学式: C₇H₁₆O₄
• 分子量: 164.202
• InChiKey: ANMKUPNQXJXFGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-dihydroperoxyheptane 、 三乙基硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以2.06 g的产率得到4,4-bis[(triethylsilyl)dioxy]heptane
  参考文献：
  名称：

  Spiro- and Dispiro-1,2-dioxolanes:  Contribution of Iron(II)-Mediated One-Electron vs Two-Electron Reduction to the Activity of Antimalarial Peroxides

  摘要：

  Fourteen spiro- and dispiro-1,2-dioxolanes were synthesized by peroxycarbenium ion annulations with alkenes in yields ranging from 30% to 94%. Peroxycarbenium ion precursors included triethylsilyldiperoxyketals and -acetals derived from geminal dihydroperoxides and from a new method employing triethylsilylperoxyketals and -acetals derived from ozonolysis of alkenes. The 1,2-dioxolanes were either inactive or orders of magnitude less potent than the corresponding 1,2,4-trioxolanes or artemisinin against P. falciparum in vitro and P. berghei in vivo. In reactions with iron(II), the predominant reaction course for 1,2-dioxolane 3a was two-electron reduction. In contrast, the corresponding 1,2,4-trioxolane 1 and the 1,2,4-trioxane artemisinin undergo primarily one-electron iron(II)-mediated reductions. The key structural element in the latter peroxides appears to be an oxygen atom attached to one or both of the peroxide-bearing carbon atoms that permits rapid beta-scission reactions (or H shifts) to form primary or secondary carbon-centered radicals rather than further reduction of the initially formed Fe(HI) complexed oxy radicals.

  DOI：

  10.1021/jm0707673
• 作为产物：
  描述：

  4-庚酮 在 双氧水 、 碘 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 4,4-dihydroperoxyheptane
  参考文献：
  名称：

  Spiro- and Dispiro-1,2-dioxolanes:  Contribution of Iron(II)-Mediated One-Electron vs Two-Electron Reduction to the Activity of Antimalarial Peroxides

  摘要：

  Fourteen spiro- and dispiro-1,2-dioxolanes were synthesized by peroxycarbenium ion annulations with alkenes in yields ranging from 30% to 94%. Peroxycarbenium ion precursors included triethylsilyldiperoxyketals and -acetals derived from geminal dihydroperoxides and from a new method employing triethylsilylperoxyketals and -acetals derived from ozonolysis of alkenes. The 1,2-dioxolanes were either inactive or orders of magnitude less potent than the corresponding 1,2,4-trioxolanes or artemisinin against P. falciparum in vitro and P. berghei in vivo. In reactions with iron(II), the predominant reaction course for 1,2-dioxolane 3a was two-electron reduction. In contrast, the corresponding 1,2,4-trioxolane 1 and the 1,2,4-trioxane artemisinin undergo primarily one-electron iron(II)-mediated reductions. The key structural element in the latter peroxides appears to be an oxygen atom attached to one or both of the peroxide-bearing carbon atoms that permits rapid beta-scission reactions (or H shifts) to form primary or secondary carbon-centered radicals rather than further reduction of the initially formed Fe(HI) complexed oxy radicals.

  DOI：

  10.1021/jm0707673

文献信息

• [EN] CETANE NUMBER IMPROVER, FUEL OIL INCLUDING THE SAME, AND TETRAOXANE-BASED COMPOUND<br/>[FR] ADDITIF PRO-CÉTANE, MAZOUT COMPRENANT LEDIT ADDITIF, ET COMPOSÉ À BASE DE TÉTRAOXANE
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2010134678A2

  公开（公告）日：2010-11-25

  Disclosed is a cetane number improver comprising a tetraoxane-based compound having a specific structure. Fuel oil comprising the cetane number improver and a novel tetraoxane-based compound are also provided. The addition of the cetane number improver to fuel oil improves the cetane number of the fuel oil. This cetane number improver has lower toxicity and superior stability, compared to a conventional cetane number improver, and can greatly improve the cetane number of fuel oil such as diesel, thereby increasing combustion efficiency of fuel oil.
• Spiro- and Dispiro-1,2-dioxolanes:  Contribution of Iron(II)-Mediated One-Electron vs Two-Electron Reduction to the Activity of Antimalarial Peroxides
  作者：Xiaofang Wang、Yuxiang Dong、Sergio Wittlin、Darren Creek、Jacques Chollet、Susan A. Charman、Josefina Santo Tomas、Christian Scheurer、Christopher Snyder、Jonathan L. Vennerstrom

  DOI：10.1021/jm0707673

  日期：2007.11.1

  Fourteen spiro- and dispiro-1,2-dioxolanes were synthesized by peroxycarbenium ion annulations with alkenes in yields ranging from 30% to 94%. Peroxycarbenium ion precursors included triethylsilyldiperoxyketals and -acetals derived from geminal dihydroperoxides and from a new method employing triethylsilylperoxyketals and -acetals derived from ozonolysis of alkenes. The 1,2-dioxolanes were either inactive or orders of magnitude less potent than the corresponding 1,2,4-trioxolanes or artemisinin against P. falciparum in vitro and P. berghei in vivo. In reactions with iron(II), the predominant reaction course for 1,2-dioxolane 3a was two-electron reduction. In contrast, the corresponding 1,2,4-trioxolane 1 and the 1,2,4-trioxane artemisinin undergo primarily one-electron iron(II)-mediated reductions. The key structural element in the latter peroxides appears to be an oxygen atom attached to one or both of the peroxide-bearing carbon atoms that permits rapid beta-scission reactions (or H shifts) to form primary or secondary carbon-centered radicals rather than further reduction of the initially formed Fe(HI) complexed oxy radicals.