methyl (R)-11-hydroperoxyoctadec-9(Z)-enoate | 144301-52-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (R)-11-hydroperoxyoctadec-9(Z)-enoate
• 英文别名: methyl (Z,11R)-11-hydroperoxyoctadec-9-enoate
• CAS: 144301-52-0
• 化学式: C₁₉H₃₆O₄
• 分子量: 328.492
• InChiKey: CUHYOWGKURCMLO-BBLCHGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  23.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (R)-11-hydroperoxyoctadec-9(Z)-enoate 在 反式-二叔丁基连二次硝酸酯 、 氧气-18O2 作用下， 以 正己烷 为溶剂， 生成 (S)-methyl 9-hydroperoxyoctadec-10(E)-enoate 、 methyl (R)-11-hydroperoxyoctadec-9(E)-enoate 、 (E)-(R)-9-Hydroperoxy-octadec-10-enoic acid methyl ester 、 methyl (S)-11-hydroperoxyoctadec-9(E)-enoate 、 C₁₉H₃₆O₂⁽¹⁸⁾O₂ 、 C₁₉H₃₆O₂⁽¹⁸⁾O₂
  参考文献：
  名称：

  An allyl radical-dioxygen caged pair mechanism for cis-allylperoxyl rearrangements

  摘要：

  DOI：

  10.1021/ja00050a076
• 作为产物：
  描述：

  methyl (Z)-11-hydroperoxyoctadec-9-enoate 生成 methyl (R)-11-hydroperoxyoctadec-9(Z)-enoate
  参考文献：
  名称：

  The Mechanism of the [3,2] Allylperoxyl Rearrangement: A Radical-Dioxygen Pair Reaction That Proceeds with Stereochemical Memory

  摘要：

  The mechanism of the [2,3] allyl hydroperoxide rearrangement was investigated. The rearrangement proceeds with stereoselectivity and is promoted by free radical initiators. Recent theoretical investigations by Boyd et. al. support a beta-fragmentation process involving an intermediate allyl radical for this rearrangement, and this mechanism was probed using solvent viscosity, isotopic labeling, and stereochemistry. These studies indicate that solvent viscosity and temperature affect the partitioning between escape and collapse of an intermediate allyl radical-dioxygen caged pair and support the dissociative mechanism. An increase in solvent viscosity results in a decrease in escape product and an identical increase in pair collapse product formed with stereocontrol.

  DOI：

  10.1021/ja00094a027