N,N-dioctadecyl-N-methyl-N-<2-nitro-5-oxidobenzyl>ammonium bromide | 128971-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N-dioctadecyl-N-methyl-N-<2-nitro-5-oxidobenzyl>ammonium bromide
• 英文别名: N,N-dioctadecyl-N-methyl-N-(2-nitro-5-oxidobenzyl)ammonium bromide；(5-Hydroxy-2-nitrophenyl)methyl-methyl-dioctadecylazanium;bromide
• CAS: 128971-01-7
• 化学式: Br*C₄₄H₈₃N₂O₃
• 分子量: 768.059
• InChiKey: GOZAZJLQDQWNRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.77
• 重原子数：
  50
• 可旋转键数：
  36
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酰氯 、 N,N-dioctadecyl-N-methyl-N-<2-nitro-5-oxidobenzyl>ammonium bromide 以 二氯甲烷 为溶剂， 反应 2.5h， 以39%的产率得到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
• 作为产物：
  描述：

  N,N-Dioctadecyl-N-methyl-N-<4-nitro-1-(benzoyloxy)-3-benzyl>ammonium bromide 在 sodium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 N,N-dioctadecyl-N-methyl-N-<2-nitro-5-oxidobenzyl>ammonium bromide
  参考文献：
  名称：

  通过自我指示的头基检测到质子/氢氧化物跨铵离子双层囊泡的渗透

  摘要：

  -硝基酚官能化的囊泡表面活性剂（2）是囊泡和囊泡表面局部pH状况的敏感，可逆和连续的报告物

  DOI：

  10.1016/s0040-4039(00)97366-0

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.
• Proton/hydroxide permeation across ammonium ion bilayer vesicles detected by self-indicating head groups
  作者：Robert A. Moss、Tsunehisa Fujita

  DOI：10.1016/s0040-4039(00)97366-0

  日期：1990.1

  -Nitrophenol-functionalized vesicular surfactants (2) are sensitive, reversible and continuous reporters of local pH conditions at endovesicular and exovesicular surfaces

  -硝基酚官能化的囊泡表面活性剂（2）是囊泡和囊泡表面局部pH状况的敏感，可逆和连续的报告物