heptadecafluorotridecanoic acid | 5522-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: heptadecafluorotridecanoic acid
• 英文别名: 5-(F-octyl)-pentanoic acid；5-Perfluoroctyl-pentansaeure；6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluorotridecanoic acid
• CAS: 5522-87-2
• 化学式: C₁₃H₉F₁₇O₂
• 分子量: 520.186
• InChiKey: NCSMRNHQLFRHSU-UHFFFAOYSA-N

物化性质

• 熔点：
  86.5-87.3 °C(Solv: carbon disulfide (75-15-0))
• 沸点：
  100 °C(Press: 0.02 Torr)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  heptadecafluorotridecanoic acid 在 氯化亚砜 作用下， 以 三氟乙酸 为溶剂， 反应 6.0h， 生成 5-(F-octyl)-pentanoyl carnitine
  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

文献信息

• 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).
• One-step preparation of 6-perfluoroalkylalkanoates of trehalose and sucrose for biomedical uses
  作者：Samir Abouhilale、Jacques Greiner、Jean G. Riess

  DOI：10.1016/0008-6215(91)84045-g

  日期：1991.6

  The Mitsunobu reaction has been used to obtain 6-polyfluoroalkanoates of alpha,alpha-trehalose and sucrose in yields of approximately 40% and approximately 25%, respectively. 6,6'-Diesters (3-6%) were formed in some reactions and a 6-ester (1.3%) of alpha-D-glucopyranosyl 3,4-anhydro-beta-D-tagatofuranoside in one reaction. The monoesters displayed strong surfactant properties, and reduced considerably the water surface and fluorocarbon/water interfacial tensions. Preliminary results on biocompatibility were encouraging, especially for the 6-esters of alpha,alpha-trehalose.
• ABOUHILALE, SAMIR;GREINER, JACQUES;RIESS, JEAN G., CARBOHYDR. RES., 212,(1991) C. 55-64
  作者：ABOUHILALE, SAMIR、GREINER, JACQUES、RIESS, JEAN G.

  DOI：——

  日期：——