toluene-4-sulfonic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester | 228570-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester
• 英文别名: TsO(CH2)3C8F17；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecane-1-ol p-toluenesulfonate；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl 4-methylbenzenesulfonate
• CAS: 228570-07-8
• 化学式: C₁₈H₁₃F₁₇O₃S
• 分子量: 632.338
• InChiKey: QGWFHYOAPHKIKU-UHFFFAOYSA-N

物化性质

• 沸点：
  393.3±42.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester 在 lithium chloride 作用下， 以 丙酮 为溶剂， 反应 19.0h， 以73%的产率得到1-chloro-3-perfluorooctylpropane
  参考文献：
  名称：

  Ionic Transformations in Extremely Nonpolar Fluorous Media:  Phase Transfer Catalysis of Halide Substitution Reactions

  摘要：

  Fluorous solutions of alkyl halides R-f8(CH2)(m)X (m = 2, 3; X = Cl, Br, I) are inert toward solid or aqueous NaCl, NaBr, and KI, but halide substitution occurs in the presence of fluorous phosphonium salts (10 mol %, 76-100 degrees C).

  DOI：

  10.1021/ol0706354
• 作为产物：
  描述：

  3-(全氟辛基)-2-碘丙醇 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 toluene-4-sulfonic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester
  参考文献：
  名称：

  Synthesis and antimicrobial activity of a perfluoroalkyl-containing quaternary ammonium salt

  摘要：

  A novel perfluoroalkyl-containing quaternary ammonium salt 5 was designed and synthesized. Consequently, the antimicrobial activities of compound 5 were measured with Escherichia coli 8099 as a Gram-negative strain and Staphylococcus aureus ATCC 6538 as a Gram-positive strain. Both the minimum inhibitory concentration (MIC, the lowest concentration of compound 5 that inhibits microbial growth) values of quaternary ammonium salt 5 against Escherichia coli 8099 and Staphylococcus aureus ATCC 6538 were 7.8 mug/ml. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00193-3

文献信息

• Synthesis of monosaccharide units using fluorous method
  作者：Kohtaro Goto、Mamoru Mizuno

  DOI：10.1016/j.tetlet.2007.06.068

  日期：2007.8

  The efficient synthesis of monosaccharide units, glycosyl acceptor, and donor, by using the fluorous tag method was achieved. Fluorous tag 5 was stable in each reaction condition to the preparation of various monosaccharide units. Each fluorous synthetic intermediate could be obtained in a straightforward manner by a simple fluorous–organic solvent partition.

  通过使用荧光标记方法，可以有效合成单糖单元，糖基受体和供体。氟标签5在每种反应条件下对于制备各种单糖单元都是稳定的。每个氟合成中间体都可以通过简单的氟-有机溶剂分配以直接方式获得。
• An effective and catalytic oxidation using recyclable fluorous IBX
  作者：Tsuyoshi Miura、Kosuke Nakashima、Norihiro Tada、Akichika Itoh

  DOI：10.1039/c0cc03149f

  日期：——

  Oxidation of alcohols in the presence of a catalytic amount of fluorous IBX and Oxone as a co-oxidant resulted in the corresponding carbonyl compounds in good to high yields. The fluorous IBX is readily recovered as insoluble fluorous IBA from the reaction mixture by simple filtration, and can be reused without significant loss of the catalytic activity.

  在催化量的氟代IBX和Oxone作为助氧化剂的存在下，醇类的氧化产生相应的羰基化合物，收率高至高。通过简单的过滤，很容易从反应混合物中将氟代IBX作为不溶性氟代IBA回收，并且可以在不显着损失催化活性的情况下重复使用。
• Fluorous Oligosaccharide Synthesis Using a Novel Fluorous Protective Group
  作者：Tsuyoshi Miura、Yuriko Hirose、Masashi Ohmae、Toshiyuki Inazu

  DOI：10.1021/ol016838o

  日期：2001.11.1

  The Bfp (bisfluorous chain type propanoyl) group, a novel fluorous protecting reagent, was able to be prepared easily. The Bfp group was readily introduced to carbohydrate, was removed in high yield, and was recyclable after cleavage. Use of the Bfp group made it possible to synthesize a tetrasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily

  Bfp（双氟链型丙酰基）是一种新型的氟保护剂，可以轻松制备。Bfp基团很容易引入碳水化合物中，以高收率除去，裂解后可回收利用。Bfp基团的使用使得可以通过最少的柱色谱纯化来合成四糖。每种合成中间体仅使用简单的氟有机溶剂萃取即可轻松纯化，并通过NMR，质谱和TLC进行监控。[结构：见文字]
• 11BETA-HALOGEN-7ALPHA-SUBSTITUTED ESTRATRIENES, METOD FOR PRODUCING PHARMACEUTICAL PREPARATIONS CONTAINING SAID 11BETA-HALOGEN-7ALPHA- SUBSTITUTED ESTRATRIENES AND USE OF THE SAME FOR PRODUCING MEDICAMENTS
  申请人：——

  公开号：US20030069434A1

  公开（公告）日：2003-04-10

  This invention describes the new 11&bgr;-halogen-7&agr;-substituted estratrienes of general formula I 1 in which R 11 is a fluorine or chlorine atom, and the other substituents have the meanings that are explained in more detail in the description. The compounds have antiestrogenic properties or tissue-selective estrogenic properties and are suitable for the production of pharmaceutical agents.

  这项发明描述了一种新的11&bgr;-卤素-7&agr;-取代的雌三烯类化合物，其一般化学式为I1，其中R11是氟或氯原子，其他取代基的含义在描述中有更详细的解释。这些化合物具有抗雌激素作用或组织选择性雌激素作用，并适用于制备药物。
• Preparation of Fluorous DMF Solvents and Their Use for Some Pd-catalyzed Cross-coupling Reactions
  作者：Hiroshi Matsubara、Louis Maeda、Ilhyong Ryu

  DOI：10.1246/cl.2005.1548

  日期：2005.11

  N,N-Dimethylformamide derivatives 1a (Rf6-DMF) and 1b (Rf8-DMF) with a C6 or C8 fluorous ponytail, respectively, have been synthesized and examined for some physical properties. Rf6-DMF was tested as a solvent for Mizoroki–Heck arylation of butyl acrylate and Sonogashira coupling reaction of iodobenzene with phenylacetylene. Both reactions proceeded as smoothly as in DMF to give the products in high yield. Fluorous DMF derivative 1a can be recovered easily from the reaction mixture by a fluorous/organic biphasic workup and recycled.

  我们合成了 N,N-二甲基甲酰胺衍生物 1a（Rf6-DMF）和 1b（Rf8-DMF），这两种衍生物分别带有 C6 或 C8 多氟马尾，并对它们的一些物理性质进行了研究。Rf6-DMF 被测试用作丙烯酸丁酯的 Mizoroki-Heck 芳基化反应和碘苯与苯乙炔的 Sonogashira 偶联反应的溶剂。这两个反应与在 DMF 中一样顺利进行，并以高产率得到产物。氟 DMF 衍生物 1a 很容易通过氟/有机双相处理从反应混合物中回收并循环使用。