1-bromo-12,12,13,13,14,14,15,15,15-nonafluoropentadecane | 213207-95-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-bromo-12,12,13,13,14,14,15,15,15-nonafluoropentadecane
• 英文别名: 1-bromo-11-(nonafluorobutyl)undecane；15-Bromo-1,1,1,2,2,3,3,4,4-nonafluoropentadecane
• CAS: 213207-95-5
• 化学式: C₁₅H₂₂BrF₉
• 分子量: 453.229
• InChiKey: HIEQJDKWJZYMQM-UHFFFAOYSA-N

物化性质

• 沸点：
  120-170 °C(Press: 0.06 Torr)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-bromo-12,12,13,13,14,14,15,15,15-nonafluoropentadecane 在 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Adsorption of Gemini Surfactants with Partially Fluorinated Chains at Three Different Surfaces: Neutron Reflectometry Results

  摘要：

  The adsorption of six symmetrical cationic (dimethylammonium bromide) gemini surfactants with four different partially fluorinated chains at three different surfaces-the air/water, the hydrophilic silica/water, and the hydrophobic (octadecyltricholorosilane (OTS))/water-has been investigated by neutron reflectometry. The corresponding single chain trimethylammonium bromides have also been studied at the two solid surfaces. Four of the geminis with a C-6 spacer and chains with differing amounts of fluorocarbon have identical limiting areas per molecule at the air/water interface (106 +/- 5 angstrom(2)). This is similar to the value for the corresponding hydrocarbon gemini with a C-6 spacer and C-12 side chains, but unlike the hydrocarbon gemini, it is significantly more than twice the area per molecule of the corresponding single chain cationic. In adsorbed aggregates on hydrophilic silica the area per molecule decreases from the air/water value by an average of about 25%, indicating a substantial improvement in the packing of these geminis in the aggregate, which can be attributed to the stronger interaction between the hydrophobic chains in the interior of the aggregates. On the hydrophobic OTS surface the area per molecule in the adsorbed monolayer for three partially fluorinated geminis decreased by about 15% from the air/water value, again indicating much more favorable packing next to the hydrophobic OTS, but for one of the geminis, fC(8)C(6)-C-6-C(6)fC(8), the change in area was reversed. This reversal is accompanied by a marked thinning of the layer, which is attributed to a shift in the balance between the interactions of the hydrocarbon spacer and fluorocarbon chain fragments and the OTS surface.

  DOI：

  10.1021/la104291w
• 作为产物：
  描述：

  10-十一烯-1-醇 在 偶氮二异丁腈 、 溴 、 三正丁基氢锡 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 27.0h， 生成 1-bromo-12,12,13,13,14,14,15,15,15-nonafluoropentadecane
  参考文献：
  名称：

  由相应的卤化物合成末端全氟化的长链烷硫醇，硫化物和二硫化物

  摘要：

  半氟化Ñ -alkanethiols，对称硫化物和二硫化物轴承链（一个或多个）F（CF 2）Ñ（CH 2）米与Ñ = 4，6，8，10，和米从相应的碘化物或溴化物开始，＝ 2、11已经通过各种合成方法制备。通常基于硫化氢钠的方法来完成这种转化，处理从硫代硫酸钠制得的邦特盐，异硫脲鎓盐的碱性水解，在温和条件下由硫代磷酸钠形成的硫代磷酸酯的水解以及硫醇乙酸的碱性水解相对于标题化合物的选择性合成，已研究并比较了其衍生物。硫代乙酸路线基本上产生带有一些二硫化物的硫醇。硫脲的结果似乎相似。硫代磷酸钠是合成硫醚的极佳途径，尤其是从溴化物开始时。基于硫化氢钠和硫代硫酸钠的两种经典方法显示出较差的选择性。有可能获得纯净状态下报告的所有硫化合物。

  DOI：

  10.1016/s0022-1139(00)00215-3

文献信息

• Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides
  作者：Sandhya M. Vyas、Jaroslav Turánek、Pavlína Knötigová、Andrea Kašná、Veronika Kvardová、Venkat Koganti、Stephen E. Rankin、Barbara L. Knutson、Hans-Joachim Lehmler

  DOI：10.1039/b516039a

  日期：——

  Although cationic surfactants are of general interest for a variety of consumer and biomedical applications, only a limited number of partially fluorinated, single-tailed, cationic surfactants have been synthesized. To study the potential usefulness of fluorinated cationic surfactants for these applications we synthesized a series of partially fluorinated pyridinium bromide surfactants. Three 10-perfluoroalkyldecyl pyridinium surfactants were synthesized by coupling a perfluoroalkyl iodide with 9-decene-1-yl acetate using an AIBN mediated radical reaction. The resulting 9-iodo-10-perfluoroalkyldec-1-yl acetates were deiodinated using HI–Zn–EtOH and hydrolyzed using KOH–EtOH to yield the corresponding 10-perfluoroalkyldecanol. The partially fluorinated alcohol was converted into the bromide using Br2–PPh3. Alkylation of excess pyridine with the bromides gave the desired 10-perfluoroalkyldecyl pyridinium bromides in good yields. Three 10-perfluoroalkylundecyl surfactants were synthesized using a similar approach with 10-undecenoic acid methyl ester as starting material. Based on an initial in vitro toxicity assessment, the toxicity of the partially fluorinated pyridinium surfactants was slightly lower or comparable to benzalkonium chloride, a typically cationic surfactant (with IC50s of tested compounds ranging from 5 to 15 μM). An increase in the length and/or the degree of fluorination of the hydrophobic tail correlated with a mild decrease of cytotoxicity and haemolytic activity. Partially fluorinated pyridinium surfactants may, therefore, be useful for biomedical applications such as components for novel gene and drug delivery systems.

  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。
• Synthesis of terminally perfluorinated long-chain alkanethiols, sulfides and disulfides from the corresponding halides
  作者：C Naud、P Calas、H Blancou、A Commeyras

  DOI：10.1016/s0022-1139(00)00215-3

  日期：2000.7

  prepared by various synthetic methods, starting from the corresponding iodides or bromides. Methods based on sodium hydrogen sulfide, commonly used to accomplish this conversion, treatment of the Bunte salt obtained from sodium thiosulfate, the basic hydrolysis of isothiouronium salts, the hydrolysis under mild conditions of thiophosphorates formed from sodium thiophosphate and the basic hydrolysis of thiol

  半氟化Ñ -alkanethiols，对称硫化物和二硫化物轴承链（一个或多个）F（CF 2）Ñ（CH 2）米与Ñ = 4，6，8，10，和米从相应的碘化物或溴化物开始，＝ 2、11已经通过各种合成方法制备。通常基于硫化氢钠的方法来完成这种转化，处理从硫代硫酸钠制得的邦特盐，异硫脲鎓盐的碱性水解，在温和条件下由硫代磷酸钠形成的硫代磷酸酯的水解以及硫醇乙酸的碱性水解相对于标题化合物的选择性合成，已研究并比较了其衍生物。硫代乙酸路线基本上产生带有一些二硫化物的硫醇。硫脲的结果似乎相似。硫代磷酸钠是合成硫醚的极佳途径，尤其是从溴化物开始时。基于硫化氢钠和硫代硫酸钠的两种经典方法显示出较差的选择性。有可能获得纯净状态下报告的所有硫化合物。
• Morita-Baylis-Hillman Reaction on Water without Organic Solvent, Assisted by a ‘Catalytic’ Amount of Amphiphilic Imidazole Derivatives
  作者：Seijiro Matsubara、Keisuke Asano

  DOI：10.1055/s-0029-1216944

  日期：2009.10

  A Morita-Baylis-Hillman (MBH) reaction using water as a solvent without any organic solvent can be performed by using an amphiphilic N-alkylimidazole. This reaction is accelerated by the addition of water and is the first example of a ‘catalytic’ MBH reaction without organic solvent in the presence of water.

  可以使用两性N-烷基咪唑在无任何有机溶剂的情况下，以水作为溶剂进行Morita-Baylis-Hillman (MBH)反应。随着水的添加，该反应得以加速，这是在水存在下进行的第一个没有有机溶剂的“催化”MBH反应的例子。
• Method of modifying a surface of a substrate and articles therefrom
  申请人：3M Innovative Properties Company

  公开号：US20040241396A1

  公开（公告）日：2004-12-02

  A method of modifying a surface of a substrate comprises: inkjet printing a material, the material comprising a non-vaporizable component onto a surface of a substrate, wherein the non-vaporizable component comprises at least one compound having the formula R f —Z—X wherein R f is a perfluoroalkyl group having from 1 to 22 carbon atoms; Z is a divalent connecting group or a covalent bond; X is selected from the group consisting of —PO 3 H, —CO 2 H, 1 and salts thereof; and wherein the compound comprises greater than 10 percent by weight of the non-vaporizable component. Various articles may be produced according to the method.

  一种修改基板表面的方法包括：将一种材料喷墨印刷到基板表面上，该材料包括一种不可蒸发组分，其中不可蒸发组分包括至少一种具有以下式子的化合物Rf—Z—X，其中Rf是具有1至22个碳原子的全氟烷基；Z是二价连接基或共价键；X选自由—PO3H，—CO2H和其盐组成的群；化合物在不可蒸发组分中的重量百分比大于10％。该方法可以生产各种物品。
• Fluorochemical treatment for silicon articles
  申请人：3M Innovative Properties Company

  公开号：US20030226818A1

  公开（公告）日：2003-12-11

  Silicon substrates having Si—H bonds are chemically modified using a fluorinated olefin having the formula: 1 wherein m is an integer greater than or equal to 1; n is an integer greater than or equal to 0; Z is a divalent linking group; and R f is a highly fluorinated organic group.

  具有Si-H键的硅衬底通过使用具有以下公式的氟代烯烃进行化学修饰：1其中m是大于或等于1的整数；n是大于或等于0的整数；Z是二价连接基团；Rf是高度氟化的有机基团。