Cyclohexyl(hydroperoxy)methyl hydroperoxide | 244237-80-7

• 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: Cyclohexyl(hydroperoxy)methyl hydroperoxide
• 英文别名: Dihydroperoxymethylcyclohexane
• CAS: 244237-80-7
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: HJUCXZXTJSKRLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  Cyclohexyl(hydroperoxy)methyl hydroperoxide 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-Cyclohexyl-6-phenyl-1,2,4,5-tetraoxane
  参考文献：
  名称：

  Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes

  摘要：

  在过氧化氢存在下，乙烯基醚 1a-c 在二乙醚中进行臭氧分解，得到相应的 1,1-双（过氧化氢）2a-c。随后进行三甲基硅烷化反应，然后在 TMSOTf 催化下与羰基化合物进行环缩合反应，得到不对称取代的 1,2,4,5-四氧杂环己烷 5-14。同样，α,α′-双（三甲基硅基过氧）醚 17 与羰基化合物反应制备出了 1,2,4,5,7-戊氧杂环烷 18 和 19。四环醚 14 在体外和体内都显示出显著的抗疟活性。

  DOI：

  10.1039/a900826h
• 作为产物：
  描述：

  亚甲基环己烷氧化物 在 双氧水 、 四氯化锡 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以54%的产率得到Cyclohexyl(hydroperoxy)methyl hydroperoxide
  参考文献：
  名称：

  Tin(IV) Chloride Promoted Reaction of Oxiranes with Hydrogen Peroxide

  摘要：

  A group of substituted oxiranes were readily transformed to the corresponding beta-hydroxyhydroperoxides (HHP) in good yields in ethereal SnCl4-H2O2 system in which SnCl4 acts as catalyst. Alternatively, treating oxiranes with SnCl4 first, followed by addition of ethereal H2O2 solution achieved primary gem-dihydroperoxides (DHP) in moderate yields. In the case of preparing DHP, SnCl4 first promoted the rearrangement of oxiranes to aldehydes, followed by condensation with hydrogen peroxide to provide DHP as final products.

  DOI：

  10.1055/s-0032-1318213

文献信息

• A simple, efficient and versatile synthesis of primary gem-dihydroperoxides from aldehydes and hydrogen peroxide
  作者：Alexander Bunge、Hans-Jürgen Hamann、Jürgen Liebscher

  DOI：10.1016/j.tetlet.2008.11.055

  日期：2009.2

  Aldehydes were efficiently converted directly into the corresponding gem-dihydroperoxides (DHPs) on treatment with aqueous 70% H2O2 in a biphasic system with ether catalyzed by camphorsulfonic acid. The synthesis represents the most versatile access to this class of compounds.

  醛被有效直接转化为相应的宝石上治疗用含水70％H -dihydroperoxides吡啶类（DHP）2 Ô 2中的两相体系与由樟脑磺酸催化的醚。合成代表了此类化合物最通用的获取途径。
• 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.
• Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes
  作者：Hye-Sook Kim、Kaoru Tsuchiya、Yasuharu Shibata、Yusuke Wataya、Yoshihiro Ushigoe、Araki Masuyama、Masatomo Nojima、Kevin J. McCullough

  DOI：10.1039/a900826h

  日期：——

  Ozonolysis of vinyl ethers 1a–c in the presence of hydrogen peroxide in diethyl ether gave the corresponding 1,1-bis(hydroperoxide)s 2a–c. Subsequent trimethylsilylation, followed by the TMSOTf-catalyzed cyclocondensation with carbonyl compounds gave the unsymmetrically-substituted 1,2,4,5-tetroxanes 5–14. Similarly, the 1,2,4,5,7-pentoxocanes 18, 19 were prepared by the reaction of an α,α′-bis(trimethylsilylperoxy) ether 17 and carbonyl compounds. The tetroxane 14 showed notable antimalarial activity in vitro and in vivo.

  在过氧化氢存在下，乙烯基醚 1a-c 在二乙醚中进行臭氧分解，得到相应的 1,1-双（过氧化氢）2a-c。随后进行三甲基硅烷化反应，然后在 TMSOTf 催化下与羰基化合物进行环缩合反应，得到不对称取代的 1,2,4,5-四氧杂环己烷 5-14。同样，α,α′-双（三甲基硅基过氧）醚 17 与羰基化合物反应制备出了 1,2,4,5,7-戊氧杂环烷 18 和 19。四环醚 14 在体外和体内都显示出显著的抗疟活性。
• Tin(IV) Chloride Promoted Reaction of Oxiranes with Hydrogen Peroxide
  作者：Chunhua Qiao、Xing Yan、Zhongwu Guo

  DOI：10.1055/s-0032-1318213

  日期：——

  A group of substituted oxiranes were readily transformed to the corresponding beta-hydroxyhydroperoxides (HHP) in good yields in ethereal SnCl4-H2O2 system in which SnCl4 acts as catalyst. Alternatively, treating oxiranes with SnCl4 first, followed by addition of ethereal H2O2 solution achieved primary gem-dihydroperoxides (DHP) in moderate yields. In the case of preparing DHP, SnCl4 first promoted the rearrangement of oxiranes to aldehydes, followed by condensation with hydrogen peroxide to provide DHP as final products.