11,11,12,12,13,13,14,14,14-nonafluoro-1-tetradecanol | 220414-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11,11,12,12,13,13,14,14,14-nonafluoro-1-tetradecanol
• 英文别名: 11,11,12,12,13,13,14,14,14-nonafluorotetradecan-1-ol；11,11,12,12,13,13,14,14,14-Nonafluorotetradecan-1-ol
• CAS: 220414-03-9
• 化学式: C₁₄H₂₁F₉O
• 分子量: 376.306
• InChiKey: TVSPAWRXGGVGQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  280.0±35.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  11,11,12,12,13,13,14,14,14-nonafluoro-1-tetradecanol 在 三乙胺 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 4.0h， 生成 11,11,12,12,13,13,14,14,14-nonafluorotetradecyl thioacetate
  参考文献：
  名称：

  末端全氟化长链烷硫醇

  摘要：

  本文描述了一系列含全氟化末端链段的链烷硫醇的合成：F（CF 2）m（CH 2）n SH，其中m  = 1，n  = 9-15；m  = 2，n  = 11-14；m  = 3，n  = 10-13；和米 = 4，Ñ  = 9-12。通式F（CF 2）m（CH 2）n I的氟化烷基碘，其中m  = 1-4和n 将= 0或1添加到在α末端被硫代乙酸酯基官能化的长链ω-烯烃。反应在自由基条件下以良好的产率进行。所得仲碘的还原得到具有全氟烷基末端链段的长链链烷硫基乙酸酯。这些中间体很容易通过酸性脱保护作用转化为相应的末端全氟链烷硫醇。使用自组装单分子层（SAM）技术，应将产物硫醇用于定义明确的氟化界面。

  DOI：

  10.1016/s0022-1139(98)00284-x
• 作为产物：
  描述：

  10-乙酰-1-癸 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 11,11,12,12,13,13,14,14,14-nonafluoro-1-tetradecanol
  参考文献：
  名称：

  末端全氟化长链烷硫醇

  摘要：

  本文描述了一系列含全氟化末端链段的链烷硫醇的合成：F（CF 2）m（CH 2）n SH，其中m  = 1，n  = 9-15；m  = 2，n  = 11-14；m  = 3，n  = 10-13；和米 = 4，Ñ  = 9-12。通式F（CF 2）m（CH 2）n I的氟化烷基碘，其中m  = 1-4和n 将= 0或1添加到在α末端被硫代乙酸酯基官能化的长链ω-烯烃。反应在自由基条件下以良好的产率进行。所得仲碘的还原得到具有全氟烷基末端链段的长链链烷硫基乙酸酯。这些中间体很容易通过酸性脱保护作用转化为相应的末端全氟链烷硫醇。使用自组装单分子层（SAM）技术，应将产物硫醇用于定义明确的氟化界面。

  DOI：

  10.1016/s0022-1139(98)00284-x

文献信息

• Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants
  作者：Xueshu Li、Jaroslav Turánek、Pavlína Knötigová、Hana Kudláčková、Josef Mašek、D. Brant Pennington、Stephen E. Rankin、Barbara L. Knutson、Hans-Joachim Lehmler

  DOI：10.1039/b805015e

  日期：——

  fluorinated non-ionic surfactants are of interest for a range of biomedical applications, such as the pulmonary administration of drugs using reverse water-in-perfluorocarbon microemulsions. We herein report the synthesis and characterization of a series of partially fluorinated β-D-glucopyranoside surfactants from the respective alcohols and peracetylated β-D-glucopyranoside using BF3·Et2O as catalyst. The

  部分氟化的非离子 表面活性剂 对于一系列生物医学应用（例如肺部给药）感兴趣 毒品使用反向在全氟化碳中的水微乳液。我们在此报告了一系列部分氟化的β- D-吡喃葡萄糖苷的合成与表征表面活性剂 从各自 酒类和BF 3 ·Et 2 O作为过乙酰化的β- D-吡喃葡萄糖苷催化剂。这表面活性剂 氟化物的填充参数 表面活性剂 范围从0.472至0.534（MOPAC计算）或0.562至0.585（根据文献值计算），与 表面活性剂具有类似的部分氟化尾巴。根据初步的生物相容性评估，β- D-吡喃葡萄糖苷表面活性剂在B16F10小鼠黑素瘤细胞系中具有低毒性，并且对兔红细胞的溶血活性相对较低。氟化的表面活性剂 与它们的细胞相比，似乎对培养的细胞毒性较小，并且具有较低的溶血活性 烃类似物。此外，氟化作用似乎同时降低了细胞毒性和溶血活性。已报道其他部分氟化物具有相似的结构-活性关系表面活性剂。总体而言，这些发现表明，表面活性剂
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  DOI：10.1016/j.jfluchem.2019.04.008

  日期：2019.6

  Fluorous gels of perfluorodecalin (PFD) were prepared using chemically synthesized fluorous gelators. To enhance the fluorophilicity of gelators, fluoroalkyl chains were introduced to the alkyl chains of known gelators. The synthesized fluoroalkyl-containing anthraquinone formed gels of PFD. The prepared gel of PFD was used for cell culture and the cytotoxicity of the gel was assessed in view of its

  使用化学合成的氟胶凝剂制备全氟萘烷（PFD）的荧光凝胶。为了增强胶凝剂的亲氟性，将氟烷基链引入已知胶凝剂的烷基链中。合成的含氟代烷基的蒽醌形成PFD凝胶。所制备的PFD凝胶用于细胞培养，并鉴于其潜在的生物医学应用对其凝胶的细胞毒性进行了评估。
• Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes
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  DOI：10.1002/adsc.202300299

  日期：2023.8.10

  The direct hydroperfluoroalkylation of a wide range of unactivated alkenes has been achieved at room temperature with readily available iodoperfluoroalkanes using 4-tert-butylcatechol as a source of hydrogen atom and triethylborane. The hydrotrifluoromethylation could also be achieved under these conditions using gaseous trifluoromethyl iodide. An experimentally simple two-step, one-pot hydrotrifluoromethylation

  使用4-叔丁基邻苯二酚作为氢原子和三乙基硼烷的来源，在室温下使用容易获得的碘全氟烷烃实现了多种未活化烯烃的直接氢全氟烷基化。加氢三氟甲基化也可以在这些条件下使用气态三氟甲基碘来实现。还开发了一种实验简单的两步一锅氢三氟甲基化工艺，使用易于使用的三氟甲磺酰氯作为三氟甲基自由基的来源。使用这两种方法，可以有效衍生化多种底物，包括类异戊二烯天然产物。
• Thermodynamic study on hydrated bilayers of ether-linked phosphatidylcholines with terminal perfluorobutyl group
  作者：Masaya Miyazaki、Chika Arisaka、Ai Nakagawara、Nanako Sasaki、Hiroshi Takahashi、Toshiyuki Takagi、Hideki Amii、Masashi Sonoyama

  DOI：10.1016/j.bbamem.2023.184261

  日期：2024.2

  liposomes aiming at applications of structural and functional analyses of membrane proteins. Differential scanning calorimetric investigations of the thermotropic transition of hydrated di-O-F4-Cn-PC bilayers demonstrated that the transition temperature of every di-O-F4-Cn-PC decreases by ~20 °C compared to their corresponding non-fluorinated PCs, di-O-Cn-PCs. With the elongation of the hydrophobic chain

  开发了具有不同烷基链长度 （di-O-F4-Cn-PCs， n = 14,16 和 18） 的新型末端含醚全氟丁基的末端全氟丁基磷脂酰胆碱作为稳定脂质体的可能材料，旨在用于膜蛋白的结构和功能分析。水合 di-O-F4-Cn-PC 双层热致变的差示扫描量热研究表明，与相应的非氟化 PCs、di-O-Cn-PCs相比，每个 di-O-F4-Cn-PC 的转变温度降低了 ~20 °C。另一方面，随着疏水链的伸长，过渡焓 （ΔH） 和熵 （ΔS） 呈线性增加。di-O-F4-Cn-PCs 和 di-O-Cn-PCs 之间 ΔH 和 ΔS 值与净烃链长度的比较强烈表明，在 di-O-F4-Cn-PC 膜的热致转变中，全氟丁基链段经历非常有限的结构变化;因此，烃段主要负责相变。
• Source of Image Contrast in STM Images of Functionalized Alkanes on Graphite:  A Systematic Functional Group Approach
  作者：Christopher L. Claypool、Francesco Faglioni、William A. Goddard、Harry B. Gray、Nathan S. Lewis、R. A. Marcus

  DOI：10.1021/jp9701799

  日期：1997.7.1

  A series of functionalized alkanes and/or alkyl alcohols have been prepared and imaged by scanning tunneling microscopy (STM) methods on graphite surfaces. The stability of these ordered overlayers has facilitated reproducible collection of STM images at room temperature with submolecular resolution, in most cases allowing identification of individual hydrogen atoms in the alkane chains, but in all cases allowing identification of molecular length features and other aspects of the image that can be unequivocally related to the presence of functional groups in the various molecules of concern. Functional groups imaged in this study include halides (X = F, Cl, Br, I), amines, alcohols, nitriles, alkenes, alkynes, ethers, thioethers, and disulfides. Except for -Cl and -OH, all of the other functional groups could be distinguished from each other and from -Cl or -OH through an analysis of their STM metrics and image contrast behavior. The dominance of molecular topography in producing the STM images of alkanes and alkanols was established experimentally and also was consistent with quantum chemistry calculations. Unlike the contrast of the methylene regions of the alkyl chains, the STM contrast produced by the various functional groups was not dominated by topographic effects, indicating that variations in local electronic coupling were important in producing the observed STM images of these regions of the molecules. For molecules in which electronic effects overwhelmed topographic effects in determining the image contrast, a simple model is presented to explain the variation in the electronic coupling component that produces the contrast between the various functional groups observed in the STM images. Additionally, the bias dependence of these STM images has been investigated and the contrast vs bias behavior is related to factors involving electron transfer and hole transfer that have been identified as potentially being important in dominating the electronic coupling in molecular electron transfer processes.