11-Hydroperoxyoctadec-9-enoic acid | 67851-50-7

• 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: 11-Hydroperoxyoctadec-9-enoic acid
• 英文别名: 11-hydroperoxyoctadec-9-enoic acid
• CAS: 67851-50-7
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: WWEFPLFGKQOHPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  油酸 在 水 、 氧气 、 rose bengal 作用下， 以 乙腈 为溶剂， 生成 9-Hydroperoxyoctadec-10-ensaure 、 11-Hydroperoxyoctadec-9-enoic acid
  参考文献：
  名称：

  Visible Light Reactive Single‐Chain Nanoparticles

  摘要：

  AbstractWe introduce a single‐chain nanoparticle (SCNP) system capable of catalyzing the photooxidation of nonpolar alkenes up to three times more efficiently than an equivalent small‐molecule photosensitizer at an identical concentration. Specifically, we construct a polymer chain constituted of poly(ethylene glycol) methyl ether methacrylate and glycidyl methacrylate which we compact via multifunctional thiol‐epoxide ligation and functionalize with Rose Bengal (RB) in a one pot reaction, affording SCNPs with a hydrophilic shell and hydrophobic photocatalytic regions. Photooxidation of the internal alkene in oleic acid proceeds under green light. RB confined within the SCNP is three times more effective for nonpolar alkenes than free RB in solution, which we hypothesize is due to the spatial proximity of the photosensitizing units to the substrate in the hydrophobic region. Our approach demonstrates that SCNP based catalysts can afford enhanced photocatalysis via confinement effects in a homogeneous reaction environment.

  DOI：

  10.1002/anie.202302995

文献信息

• Visible Light Reactive Single‐Chain Nanoparticles
  作者：Kai Mundsinger、Bryan T. Tuten、Lily Wang、Kira Neubauer、Christian Kropf、Megan L. O'Mara、Christopher Barner-Kowollik

  DOI：10.1002/anie.202302995

  日期：——

  AbstractWe introduce a single‐chain nanoparticle (SCNP) system capable of catalyzing the photooxidation of nonpolar alkenes up to three times more efficiently than an equivalent small‐molecule photosensitizer at an identical concentration. Specifically, we construct a polymer chain constituted of poly(ethylene glycol) methyl ether methacrylate and glycidyl methacrylate which we compact via multifunctional thiol‐epoxide ligation and functionalize with Rose Bengal (RB) in a one pot reaction, affording SCNPs with a hydrophilic shell and hydrophobic photocatalytic regions. Photooxidation of the internal alkene in oleic acid proceeds under green light. RB confined within the SCNP is three times more effective for nonpolar alkenes than free RB in solution, which we hypothesize is due to the spatial proximity of the photosensitizing units to the substrate in the hydrophobic region. Our approach demonstrates that SCNP based catalysts can afford enhanced photocatalysis via confinement effects in a homogeneous reaction environment.