11-(F-hexyl)-undecanoic acid | 1584-32-3

• 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: 11-(F-hexyl)-undecanoic acid
• 英文别名: 12,12,13,13,14,14,15,15,15,16,16,17,17,17-tridecafluorheptadecansaeure；tridecafluoroheptadecanoic acid；1-(Perfluorohexyl)undecanoic acid；acide 12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoique；12,12,13,13,14,14,15,15,16,16,17,17,17-Tridecafluor-heptadecansaeure-(1)；11-perfluorohexyl-undecanoic acid；11-(Tridecafluorohexyl)undecanoic acid；12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecanoic acid
• CAS: 1584-32-3
• 化学式: C₁₇H₂₁F₁₃O₂
• 分子量: 504.332
• InChiKey: IUYWORIEGOJSPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  11-(F-hexyl)-undecanoic acid 在 氯化亚砜 作用下， 以91%的产率得到11-(全氟己基)十一烷酰氯
  参考文献：
  名称：

  Synthesis of perfluoroalkylated xylitol ethers and esters: new surfactants for biomedical uses

  摘要：

  New, well-defined surfactants and cosurfactants were synthesized with the objective of enhancing the stability of fluorocarbon emulsions destined to serve as oxygen carriers for biomedical applications. Monoperfluoroalkylated ethers of xylitol were achieved by addition of perfluoroalkyl iodide on the double bond of a protected xylitol allyl ether in a one-step addition-elimination reaction. Monoesters were obtained specifically on position 5 by treating 1,2:3,4-di-O-isopropylidenexylitol with perfluoroalkylated acid chlorides of various chain lengths in pyridine at room temperature. The products display strong surface activity and produce a remarkable synergistic stabilization of a fluorocarbon/Pluronic F-68 type emulsion. Biocompatibility data are reported, which include in vitro toxicity tests on Namalva cell cultures and hemolysis tests on human blood cells; the latter was found to decrease as the length of the F-alkyl chain increased. IV injection in mice (n = 10) showed that these products were innocuous at 400-1000 mg/kg of body weight. Preliminary exchange-perfusion experiments on rats with an emulsion containing the F-octyl xylitol ether were encouraging.

  DOI：

  10.1021/jm00166a028
• 作为产物：
  描述：

  10-烯酸甲酯 在 氢氧化钾 、 偶氮二异丁腈 、 氢碘酸 、 锌 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 11-(F-hexyl)-undecanoic acid
  参考文献：
  名称：

  Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

  摘要：

  尽管阳离子表面活性剂在多种消费品和生物医学应用中备受关注，但只有有限数量的部分氟化、单尾、阳离子表面活性剂被合成出来。为了研究氟化阳离子表面活性剂在这些应用中的潜在用途，我们合成了一系列部分氟化的吡啶溴盐表面活性剂。通过使用AIBN介导的自由基反应，将全氟烷基碘与9-癸烯-1-基乙酸酯偶联，合成了三种10-全氟烷基癸基吡啶溴盐表面活性剂。所得的9-碘-10-全氟烷基癸-1-基乙酸酯通过HI-Zn-EtOH去碘化并使用KOH-EtOH水解，生成相应的10-全氟烷基癸醇。部分氟化的醇通过Br2-PPh3转化为溴化物。使用过量吡啶与溴化物烷基化，以良好产率得到了所需的10-全氟烷基癸基吡啶溴盐。使用类似的方法，以10-十一碳烯酸甲酯为起始材料，合成了三种10-全氟烷基十一烷基表面活性剂。基于初步体外毒性评估，部分氟化吡啶阳离子表面活性剂的毒性略低或与典型的阳离子表面活性剂苯扎氯铵相当（测试化合物的IC50值在5至15μM范围内）。疏水尾部的长度和/或氟化程度的增加与细胞毒性和溶血活性轻微降低相关。因此，部分氟化的吡啶阳离子表面活性剂可能对生物医学应用有益，如作为新型基因和药物递送系统的组分。

  DOI：

  10.1039/b516039a

文献信息

• Fluorous enzymatic synthesis of phosphatidylinositides
  作者：Weigang Huang、Angela Proctor、Christopher E. Sims、Nancy L. Allbritton、Qisheng Zhang

  DOI：10.1039/c4cc00022f

  日期：——

  A fluorous tagging strategy coupled with enzymatic synthesis is introduced to efficiently synthesize multiple phosphatidylinositides, which are then directly immobilized on a fluorous polytetrafluoroethylene (PTFE) membrane to probe protein-lipid interactions.

  引入了与酶促合成相结合的含氟标记策略以有效合成多种磷脂酰肌醇，然后将其直接固定在含氟聚四氟乙烯 (PTFE) 膜上以探测蛋白质-脂质相互作用。
• Enzymatic production and physicochemical characterization of uncommon wax esters and monoglycerides
  作者：Raimund Multzsch、Wolfram Lokotsch、Beate Steffen、Siegmund Lang、Jürgen O. Metzger、Hans J. Schäfer、Siegfried Warwel、Fritz Wagner

  DOI：10.1007/bf02541428

  日期：1994.7

  Wax esters from fatty alcohols and uncommon fatty acids were synthesized in yields up to 90% when commercially available microbial lipases fromRhizomucor miehei (Lipozyme^™) andCandida antarctica (SP 435) were used with limited water content in nonpolar solvents under mild conditions. The corresponding fatty acids were prepared by chemical conversion of naturally occurring resources (agricultural surpluses). Also, when phenylboronic acid was added as solubilizing agent in a nonpolar solvent, the direct enzymatic monoacylation of glycerol with uncommon fatty acids was successful. The measurement of π/A‐isotherms by means of a Langmuir film balance indicated medium film pressures, medium or large molecular areas, and interesting phase behavior. The monolayer of a wax ester at the air/water interface could be directly visualized by Brewster angle microscopy.

  摘要 在温和条件下的非极性溶剂中，使用市售的微生物脂肪酶（Rhizomucor miehei (Lipozyme™) 和 Candida antarctica (SP 435)）和有限的含水量，从脂肪醇和不常见的脂肪酸合成蜡酯，产率高达 90%。相应的脂肪酸是通过天然资源（农业剩余物）的化学转化制备的。此外，在非极性溶剂中加入苯硼酸作为增溶剂时，甘油与非常见脂肪酸的直接酶促单乙酰化也获得了成功。通过朗缪尔薄膜天平测量 π/A 等温线，结果表明薄膜压力适中，分子面积中等或较大，相行为有趣。空气/水界面上的蜡酯单层可通过布儒斯特角显微镜直接观察到。
• Metzger, Juergen O.; Linker, Ursula, Liebigs Annalen der Chemie, 1992, # 3, p. 209 - 216
  作者：Metzger, Juergen O.、Linker, Ursula

  DOI：——

  日期：——
• Long Chain Alkanoic and Alkenoic Acids with Perfluoroalkyl Terminal Segments¹
  作者：Neal O. Brace

  DOI：10.1021/jo01059a090

  日期：1962.12
• 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.