5-(F-octyl)-pentanoyl chloride | 137204-58-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 5-(F-octyl)-pentanoyl chloride
• 英文别名: 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluorotridecanoyl chloride
• CAS: 137204-58-1
• 化学式: C₁₃H₈ClF₁₇O
• 分子量: 538.632
• InChiKey: IECYDPSEHWBWPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(F-octyl)-pentanoyl chloride 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 50.0h， 生成 N,N-dimethyl 5-(F-octyl)-pentylamine
  参考文献：
  名称：

  Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

  摘要：

  Two methods for synthesizing tertiary F-alkylated amines are reported. The more general method allows the access in 56-87% yields to various NN-dialkyl F-alkyl amines. These amines are key intermediates leading in 52-96% yields to several families of surfactants, including zwitterionic and cationic derivatives and amine oxides, potentially useful in the formulation of fluorocarbon emulsions for diagnostic and therapeutic uses. The toxicity of the new surfactants and the influence of the polar head were assessed: the long chain compounds (8, 9 and 10) were found to be toxic for cell cultures and the zwitterionic compounds (7b and 8) have a LD50 < 250 mg.kg bw-1 in mice. The hemolysis test highlights the influence of the polar head: the zwitterionic compounds (7 and 8) were found to be non-hemolytic even at remarkably high concentrations (100 g l-1 for 8), whereas the cationic compounds 9 are highly hemolytic even at very low concentrations (0.05 g l-1).

  DOI：

  10.1016/0223-5234(92)90020-2
• 作为产物：
  描述：

  heptadecafluorotridecanoic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成 5-(F-octyl)-pentanoyl chloride
  参考文献：
  名称：

  Synthesis and preliminary evaluation of perfluoroalkylacyl carnitines as surfactants for biomedical use

  摘要：

  A series of acyl carnitines, 4 of which bearing a terminal perfluoroalkyl fragment, was obtained from carnitine in one step in a high grade of purity in yields ranging from 44-81%. The F-alkyl derivatives display high solubilities in water, strong surface activity and a significant emulsifying power towards fluorocarbons in water. In spite of their strong surface activity, all the biocompatibility tests performed (in vitro toxicity on Namalva cells cultures, hemolysis on human red blood cells, and iv injections in mice) indicate a significantly better biological tolerance than their hydrocarbon analogs, provided the F-alkyl moiety is larger than the alkyl moiety in the hydrophobic tail.

  DOI：

  10.1016/0223-5234(91)90138-d