3,3-dibutyl-2-oxy-3H-isoindol-5-ol | 1192487-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,3-dibutyl-2-oxy-3H-isoindol-5-ol
• CAS: 1192487-23-2
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: JXVKQYZBCZLCNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,3-dibutyl-2,3-dihydro-1H-isoindol-5-ol 在 sodium tungstate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以61%的产率得到3,3-dibutyl-2-oxy-3H-isoindol-5-ol
  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

文献信息

• Synthesis of a mitochondria-targeted spin trap using a novel Parham-type cyclization
  作者：Caroline Quin、Jan Trnka、Alison Hay、Michael P. Murphy、Richard C. Hartley

  DOI：10.1016/j.tet.2009.07.081

  日期：2009.9

  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.