{4-[3'-(hydroxymethyl)-4'-nitrophenoxy]butyl}triphenylphosphonium bromide | 1354033-67-2

• 英文名称: {4-[3'-(hydroxymethyl)-4'-nitrophenoxy]butyl}triphenylphosphonium bromide
• CAS: 1354033-67-2
• 化学式: Br*C₂₉H₂₉NO₄P
• 分子量: 566.431
• InChiKey: LHHLGTVWFYBLQV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {4-[3'-(hydroxymethyl)-4'-nitrophenoxy]butyl}triphenylphosphonium bromide 、 2,4-二硝基氟苯 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到{4-[3'-(2'',4''-dinitrophenoxymethyl)-4'-nitrophenoxy]butyl}triphenylphosphonium bromide
  参考文献：
  名称：

  Selective Uncoupling of Individual Mitochondria within a Cell Using a Mitochondria-Targeted Photoactivated Protonophore

  摘要：

  Depolarization of an individual mitochondrion or small clusters of mitochondria within cells has been achieved using a photoactivatable probe. The probe is targeted to the matrix of the mitochondrion by an alkyltriphenylphosphonium lipophilic cation and releases the protonophore 2,4-dinitrophenol locally in predeter mined regions in response to directed irradiation with UV light via a local photolysis system. This also provides a proof of principle for the general temporally and spatially controlled release of bioactive molecules, pharmacophores, or toxins to mitochondria with tissue, cell, or mitochondrion specificity.

  DOI：

  10.1021/ja2077922
• 作为产物：
  描述：

  5-(4'-bromobutoxy)-2-nitrobenzaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 {4-[3'-(hydroxymethyl)-4'-nitrophenoxy]butyl}triphenylphosphonium bromide
  参考文献：
  名称：

  Selective Uncoupling of Individual Mitochondria within a Cell Using a Mitochondria-Targeted Photoactivated Protonophore

  摘要：

  Depolarization of an individual mitochondrion or small clusters of mitochondria within cells has been achieved using a photoactivatable probe. The probe is targeted to the matrix of the mitochondrion by an alkyltriphenylphosphonium lipophilic cation and releases the protonophore 2,4-dinitrophenol locally in predeter mined regions in response to directed irradiation with UV light via a local photolysis system. This also provides a proof of principle for the general temporally and spatially controlled release of bioactive molecules, pharmacophores, or toxins to mitochondria with tissue, cell, or mitochondrion specificity.

  DOI：

  10.1021/ja2077922