N,N-dimethyl-2-(perfluorohexyl)ethylamine | 84070-78-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-2-(perfluorohexyl)ethylamine
• 英文别名: N,N-dimethyl 2-(F-hexyl)-ethyl amine；3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-N,N-dimethyloctan-1-amine
• CAS: 84070-78-0
• 化学式: C₁₀H₁₀F₁₃N
• 分子量: 391.175
• InChiKey: MVGNFNKGSQBUGR-UHFFFAOYSA-N

物化性质

• 沸点：
  165.2±40.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  sodium monochloroacetic acid 、 N,N-dimethyl-2-(perfluorohexyl)ethylamine 以 异丙醇 为溶剂， 反应 192.0h， 以70%的产率得到N,N-dimethyl, N-(2-F-hexyl ethyl) ammonioacetate
  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：

  聚合甲醛 、 3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛烷胺 在 溶剂黄146 作用下， 生成 N,N-dimethyl-2-(perfluorohexyl)ethylamine
  参考文献：
  名称：

  Enhanced activity of fluorinated quaternary ammonium surfactants against Pseudomonas aeruginosa

  摘要：

  A novel series of fluorinated quaternary bisammonium surfactants has been synthesized in view to optimize their antimicrobial activities against Pseudomonas aeruginosa. As compared with commercial references, most of the new surfactants synthesized exhibit an enhanced activity which is discussed as a function of the nature of the spacer group between the quaternized nitrogen atoms and of the nature of the connector function between the nitrogen atoms and the perfluorinated carbon chains. It appears that the fluorinated "Gemini" surfactants bearing an amide connector can be an interesting alternative to hydrocarbon ammonium salts as preservatives and disinfectants against R aeruginosa. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.07.032

文献信息

• Preparation and antimicrobial behaviour of gemini fluorosurfactants
  作者：Lionel Massi、Frédéric Guittard、Richard Levy、Yves Duccini、Serge Géribaldi

  DOI：10.1016/s0223-5234(03)00059-x

  日期：2003.5

  The introduction of perfluorinated chains in the molecular structure of quaternary ammonium gemini surfactants have led to particularly active antimicrobial agents evaluated in this work. Connectors and spacers were studied in relation with antimicrobial activity in order to determine which molecular parameters are 'critical' for biological activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Nivet J.-B., Le Blanc M., Haddach M., Lanier M., Pastor R., Riess J. G., New J. Chem, 18 (1994) N 7, S 861-869
  作者：Nivet J.-B., Le Blanc M., Haddach M., Lanier M., Pastor R., Riess J. G.

  DOI：——

  日期：——
• Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines
  作者：JB Nivet、R Bernelin、M Le Blanc、JG Riess

  DOI：10.1016/0223-5234(92)90020-2

  日期：1992.12

  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).
• Enhanced activity of fluorinated quaternary ammonium surfactants against Pseudomonas aeruginosa
  作者：Lionel Massi、Frederic Guittard、Richard Levy、S. Géribaldi

  DOI：10.1016/j.ejmech.2008.07.032

  日期：2009.4

  A novel series of fluorinated quaternary bisammonium surfactants has been synthesized in view to optimize their antimicrobial activities against Pseudomonas aeruginosa. As compared with commercial references, most of the new surfactants synthesized exhibit an enhanced activity which is discussed as a function of the nature of the spacer group between the quaternized nitrogen atoms and of the nature of the connector function between the nitrogen atoms and the perfluorinated carbon chains. It appears that the fluorinated "Gemini" surfactants bearing an amide connector can be an interesting alternative to hydrocarbon ammonium salts as preservatives and disinfectants against R aeruginosa. (c) 2008 Elsevier Masson SAS. All rights reserved.