6,6-dihydroperoxyundecane

• 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: 6,6-dihydroperoxyundecane
• 英文别名: 6,6-Dihydroperoxyundecane
• 化学式: C₁₁H₂₄O₄
• 分子量: 220.309
• InChiKey: LCIYLKBJVFXWJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  10
• 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：

  6,6-dihydroperoxyundecane 在 硫酸 、 水 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 二正戊基酮
  参考文献：
  名称：

  A new property of geminal bishydroperoxides: Hydrolysis with the removal of hydroperoxide groups to form a ketone

  摘要：

  A new property of geminal bishydroperoxide was discovered: the ability to hydrolyze in acid medium in the presence of hydrogen peroxide with the formation of ketones. The most resistant to hydrolysis are the cyclic C(6)-bishydroperoxydes: at room temperature within one day they are practically not hydrolyzed; less stable is bishydroperoxycycloheptane (C(7)): in a day its one fifth part is hydrolyzed. Bishydroperoxydes with the cycles of C(8) and C(12) for the same time hydrolyzed to 80 and 90% respectively. Of the two linear bishydroperoxydes, 2,2-dihydroperoxydecane, with sterically unhindered center, is more resistant to hydrolysis than 6,6-dihydroperoxyundecane.

  DOI：

  10.1134/s1070363210080165
• 作为产物：
  描述：

  二正戊基酮 在 硫酸 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以43%的产率得到6,6-dihydroperoxyundecane
  参考文献：
  名称：

  通过酮与过氧化氢反应方便合成双氢过氧化物

  摘要：

  摘要 开发了一种通过硫酸催化酮与过氧化氢在 THF 中反应合成双氢过氧化物的简便方法。Gem-双氢过氧化物由五至七元环烷酮反应制备，无需额外纯化，产率 80-95%，纯度超过 95%；他们的无环类似物的产率为 43-72%。

  DOI：

  10.1080/00397910701226384

文献信息

• Synthesis and Antimalarial Activity of Novel Medium-Sized 1,2,4,5-Tetraoxacycloalkanes
  作者：Hye-Sook Kim、Yukiko Nagai、Kanako Ono、Khurshida Begum、Yusuke Wataya、Yoshiaki Hamada、Kaoru Tsuchiya、Araki Masuyama、Masatomo Nojima、Kevin J. McCullough

  DOI：10.1021/jm010026g

  日期：2001.7.1

  CsOH- or Ag2O-mediated cycloalkylation of (alkylidene)bisperoxides 3 and 1,n.-dihaloalkanes (n = 3-8) provided the corresponding medium-sized 1,2,4,5-tetraoxacycloalkanes 4-8 in moderate yields. Subsequent evaluation of the antimalarial activity of the cyclic peroxides 4-8 in vitro and in vivo revealed that 1,2,6,7-tetraoxaspiro [7.11]nonadecane 4a has considerable potential as a new, inexpensive, and potent antimalarial drug.
• A new property of geminal bishydroperoxides: Hydrolysis with the removal of hydroperoxide groups to form a ketone
  作者：A. O. Terent’ev、O. B. Krivykh、I. B. Krylov、Yu. N. Ogibin、G. I. Nikishin

  DOI：10.1134/s1070363210080165

  日期：2010.8

  A new property of geminal bishydroperoxide was discovered: the ability to hydrolyze in acid medium in the presence of hydrogen peroxide with the formation of ketones. The most resistant to hydrolysis are the cyclic C(6)-bishydroperoxydes: at room temperature within one day they are practically not hydrolyzed; less stable is bishydroperoxycycloheptane (C(7)): in a day its one fifth part is hydrolyzed. Bishydroperoxydes with the cycles of C(8) and C(12) for the same time hydrolyzed to 80 and 90% respectively. Of the two linear bishydroperoxydes, 2,2-dihydroperoxydecane, with sterically unhindered center, is more resistant to hydrolysis than 6,6-dihydroperoxyundecane.
• Convenient Synthesis of Geminal Bishydroperoxides by the Reaction of Ketones with Hydrogen Peroxide
  作者：A. O. Terent'ev、M. M. Platonov、Y. N. Ogibin、G. I. Nikishin

  DOI：10.1080/00397910701226384

  日期：2007.4.1

  Abstract A convenient procedure was developed for the synthesis of geminal bishydroperoxides by the sulfuric acid–catalyzed reaction of ketones with hydrogen peroxide in THF. Gem‐bishydroperoxides were prepared by the reactions of five‐ to seven‐membered cycloalkanones without additional purification in 80–95% yields with a purity of more than 95%; their acyclic analogs were prepared in 43–72% yields

  摘要 开发了一种通过硫酸催化酮与过氧化氢在 THF 中反应合成双氢过氧化物的简便方法。Gem-双氢过氧化物由五至七元环烷酮反应制备，无需额外纯化，产率 80-95%，纯度超过 95%；他们的无环类似物的产率为 43-72%。