N,N-dioctadecyl-N-methyl-N-<2-nitro-5-(2-picolinoyloxy)benzyl>ammonium bromide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: N,N-dioctadecyl-N-methyl-N-<2-nitro-5-(2-picolinoyloxy)benzyl>ammonium bromide
• 英文别名: N,N-dioctadecyl-N-methyl-N-[2-nitro-5-(2-picolinoyloxy)benzyl]ammonium bromide；Methyl-[[2-nitro-5-(pyridine-2-carbonyloxy)phenyl]methyl]-dioctadecylazanium;bromide
• 化学式: Br*C₅₀H₈₆N₃O₄
• 分子量: 873.155
• InChiKey: IBAISZRZAZFWOW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  12.68
• 重原子数：
  58
• 可旋转键数：
  39
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-dioctadecyl-N-methyl-N-<2-nitro-5-(2-picolinoyloxy)benzyl>ammonium bromide 在 Cu(II) ions 、 水 作用下， 生成 2-吡啶甲酸 、 4-methyl-2-(2-methyl-2-octadecylicosyl)-1-(2l5-propa-1,2-dien-2-yl)benzene
  参考文献：
  名称：

  A hydrolytic reporter of copper(II) availability in artificial liposomes

  摘要：

  The dioctadecyl ammonium surfactant 1, functionalized with a p-nitrophenyl ester of picolinic acid, has been synthesized and its hydrolysis in covesicular blends of nonfunctional surfactants dihexadecyldimethylammonium bromide, 3, dioctadecyldimethylammonium bromide, 4, and racemic 1,2-bis(palmitoyloxy)-3-(trimethylammonium)propyl bromide, 5, studied after addition of Cu(II) ions at pH = 5.0 and different temperatures. The cleavage of 1 gives the p-nitrophenoxide surfactant 2, which shows a strong absorption band at 400 nm. Clear biphasic kinetics were observed for all vesicular systems at a temperature below the gel-to-liquid crystal phase transition temperature (T(c)) of the membrane: the first, faster process (almost-equal-to 60% of the ester cleaved) was associated with the Cu(II)-catalyzed hydrolysis of the exovesicular ester; the slower one (the remaining almost-equal-to 40% of the ester cleaved) was associated with the uncatalyzed hydrolysis of the endovesicular ester. Above T(c) only a monoexponential process was observed. Variable temperature experiments allowed one to conclude that the cationic vesicles studied are totally impermeable to Cu(II) ions either below or above their T(c) which controls the rate of the transbilayer movements of the lipids.

  DOI：

  10.1021/jo00063a020
• 作为产物：
  描述：

  3-methyl-4-nitrophenyl acetate 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 氢溴酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 77.5h， 生成 N,N-dioctadecyl-N-methyl-N-<2-nitro-5-(2-picolinoyloxy)benzyl>ammonium bromide
  参考文献：
  名称：

  A hydrolytic reporter of copper(II) availability in artificial liposomes

  摘要：

  The dioctadecyl ammonium surfactant 1, functionalized with a p-nitrophenyl ester of picolinic acid, has been synthesized and its hydrolysis in covesicular blends of nonfunctional surfactants dihexadecyldimethylammonium bromide, 3, dioctadecyldimethylammonium bromide, 4, and racemic 1,2-bis(palmitoyloxy)-3-(trimethylammonium)propyl bromide, 5, studied after addition of Cu(II) ions at pH = 5.0 and different temperatures. The cleavage of 1 gives the p-nitrophenoxide surfactant 2, which shows a strong absorption band at 400 nm. Clear biphasic kinetics were observed for all vesicular systems at a temperature below the gel-to-liquid crystal phase transition temperature (T(c)) of the membrane: the first, faster process (almost-equal-to 60% of the ester cleaved) was associated with the Cu(II)-catalyzed hydrolysis of the exovesicular ester; the slower one (the remaining almost-equal-to 40% of the ester cleaved) was associated with the uncatalyzed hydrolysis of the endovesicular ester. Above T(c) only a monoexponential process was observed. Variable temperature experiments allowed one to conclude that the cationic vesicles studied are totally impermeable to Cu(II) ions either below or above their T(c) which controls the rate of the transbilayer movements of the lipids.

  DOI：

  10.1021/jo00063a020

文献信息

• A hydrolytic reporter of copper(II) availability in artificial liposomes
  作者：Giovanna Ghirlanda、Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo00063a020

  日期：1993.5

  The dioctadecyl ammonium surfactant 1, functionalized with a p-nitrophenyl ester of picolinic acid, has been synthesized and its hydrolysis in covesicular blends of nonfunctional surfactants dihexadecyldimethylammonium bromide, 3, dioctadecyldimethylammonium bromide, 4, and racemic 1,2-bis(palmitoyloxy)-3-(trimethylammonium)propyl bromide, 5, studied after addition of Cu(II) ions at pH = 5.0 and different temperatures. The cleavage of 1 gives the p-nitrophenoxide surfactant 2, which shows a strong absorption band at 400 nm. Clear biphasic kinetics were observed for all vesicular systems at a temperature below the gel-to-liquid crystal phase transition temperature (T(c)) of the membrane: the first, faster process (almost-equal-to 60% of the ester cleaved) was associated with the Cu(II)-catalyzed hydrolysis of the exovesicular ester; the slower one (the remaining almost-equal-to 40% of the ester cleaved) was associated with the uncatalyzed hydrolysis of the endovesicular ester. Above T(c) only a monoexponential process was observed. Variable temperature experiments allowed one to conclude that the cationic vesicles studied are totally impermeable to Cu(II) ions either below or above their T(c) which controls the rate of the transbilayer movements of the lipids.