[4-(3',3'-dibutyl-2'-oxy-3'h-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide | 1192487-14-1

• 英文名称: [4-(3',3'-dibutyl-2'-oxy-3'h-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide
• 英文别名: MitoSpin
• CAS: 1192487-14-1
• 化学式: Br*C₃₈H₄₅NO₂P
• 分子量: 658.659
• InChiKey: HOVLVERAMMBHAG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  35.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [4-(3',3'-dibutyl-2'-oxy-3'h-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide 在 双氧水 、 iron(II) sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 MitoSpinox
  参考文献：
  名称：

  Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization

  摘要：

  A new cyclic nitrone spin trap, [4-(3'.3'-dibutyl-2'-oxy-3'H-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide (MitoSpin), bearing a lipophilic cation has been prepared by a route that involves a novel Parham-type lithiation-cyclization of an isocyanate to give the isoindolinone core. MitoSpin accumulates in a membrane potential dependent way in energized mitochondria and its oxidation could potentially be used in the study of oxidative stress resulting from reactive oxygen species generated in mitochondria. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.081
• 作为产物：
  描述：

  3,3-dibutyl-2-oxy-3H-isoindol-5-ol 、 (4-溴丁基)三苯基溴化膦 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以24%的产率得到[4-(3',3'-dibutyl-2'-oxy-3'h-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide
  参考文献：
  名称：

  Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization

  摘要：

  A new cyclic nitrone spin trap, [4-(3'.3'-dibutyl-2'-oxy-3'H-isoindol-5'-yloxy)butyl]triphenylphosphonium bromide (MitoSpin), bearing a lipophilic cation has been prepared by a route that involves a novel Parham-type lithiation-cyclization of an isocyanate to give the isoindolinone core. MitoSpin accumulates in a membrane potential dependent way in energized mitochondria and its oxidation could potentially be used in the study of oxidative stress resulting from reactive oxygen species generated in mitochondria. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.081