P-(formylmethyl)triphenylphosphonium cation | 47181-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: P-(formylmethyl)triphenylphosphonium cation
• 英文别名: (Formylmethyl)triphenylphosphonium；Formyl-methyl-triphenylphosphonium；(2-Oxoethyl)(triphenyl)phosphonium；2-oxoethyl(triphenyl)phosphanium
• CAS: 47181-98-6
• 化学式: C₂₀H₁₈OP
• 分子量: 305.336
• InChiKey: FUCSWGRAIIZMAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  P-(formylmethyl)triphenylphosphonium cation 在 base 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 甲酰甲撑基三苯基磷
  参考文献：
  名称：

  The extremely low intrinsic reactivity of the P-(formylmethyl)triphenylphosphonium cation: an artefact due to strong covalent hydration of the carbonyl group

  摘要：

  发现标题阳离子表现出迄今为止已知的碳酸最低的 Marcus 固有反应性；这种情况反映了醛官能团的限速水合/脱水反应。

  DOI：

  10.1039/a903667i

文献信息

• Triphenylphosphonium-desferrioxamine as a candidate mitochondrial iron chelator
  作者：Roxana Y. P. Alta、Hector A. Vitorino、Dibakar Goswami、M. Terêsa Machini、Breno P. Espósito

  DOI：10.1007/s10534-017-0039-5

  日期：2017.10

  Cell-impermeant iron chelator desferrioxamine (DFO) can have access to organelles if appended to suitable vectors. Mitochondria are important targets for the treatment of iron overload-related neurodegenerative diseases. Triphenylphosphonium (TPP) is a delocalized lipophilic cation used to ferry molecules to mitochondria. Here we report the synthesis and characterization of the conjugate TPP-DFO as a mitochondrial iron chelator. TPP-DFO maintained both a high affinity for iron and the antioxidant activity when compared to parent DFO. TPP-DFO was less toxic than TPP alone to A2780 cells (IC50 = 135.60 +/- 1.08 and 4.34 +/- 1.06 mu mol L-1, respectively) and its native fluorescence was used to assess its mitochondrial localization (Rr = +0.56). These results suggest that TPP-DFO could be an interesting alternative for the treatment of mitochondrial iron overload e.g. in Friedreich's ataxia.
• The extremely low intrinsic reactivity of the P-(formylmethyl)triphenylphosphonium cation: an artefact due to strong covalent hydration of the carbonyl group
  作者：G. Moutiers、Y. X. Peng、A. Peignieux、M. J. Pouet、F. Terrier

  DOI：10.1039/a903667i

  日期：——

  The title cation is found to exhibit the lowest Marcus intrinsic reactivity known so far for a carbon acid; this situation is shown to reflect a rate-limiting hydration/dehydration reaction of the aldehyde functionality.

  发现标题阳离子表现出迄今为止已知的碳酸最低的 Marcus 固有反应性；这种情况反映了醛官能团的限速水合/脱水反应。