1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid quinolin-8-yl ester | 689247-75-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid quinolin-8-yl ester
• 英文别名: Quinolin-8-yl 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate
• CAS: 689247-75-4
• 化学式: C₁₇H₆F₁₇NO₃S
• 分子量: 627.278
• InChiKey: DWMUEDHBUIWEII-UHFFFAOYSA-N

物化性质

• 沸点：
  400.8±45.0 °C(Predicted)
• 密度：
  1.693±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid quinolin-8-yl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 甲酸 、 potassium carbonate 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 0.33h， 以79%的产率得到喹啉
  参考文献：
  名称：

  A traceless perfluorooctylsulfonyl tag for deoxygenation of phenols under microwave irradiation

  摘要：

  The perfluorooctylsulfonyl group is introduced as a traceless tag for solution-phase palladium-catalyzed deoxygenation reactions. The synthetic efficiency is improved by microwave irradiation for reaction and fluorous solid-phase extraction for separation. Further application of this traceless tag for multistep synthesis of substituted hydantoin and pyrimidine is also described. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.115
• 作为产物：
  描述：

  8-羟基喹啉 、 全氟辛基磺酰氟 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid quinolin-8-yl ester
  参考文献：
  名称：

  芳基全氟辛基磺酸酯与硼酸的高效微波辅助铃木偶联反应。

  摘要：

  [反应：见正文]通过将快速微波反应与容易的荧光分离相结合，提出了一种提高铃木偶联反应效率的新策略。在常规微波条件下，将衍生自相应酚的芳基全氟辛基磺酸酯与芳基硼酸偶合形成联芳基。中间体和产物均通过在FluoroFlash硅胶上进行固相萃取来纯化。还描述了该标签策略在联芳基取代的乙内酰脲的多步合成中的应用。

  DOI：

  10.1021/ol0496428

文献信息

• Palladium-catalyzed Buchwald–Hartwig type amination of fluorous arylsulfonates
  作者：Wei Zhang、Tadamichi Nagashima

  DOI：10.1016/j.jfluchem.2005.11.006

  日期：2006.5

  Palladium-catalyzed cross-coupling reactions of aryl perfluorooctanesulfonates with amines are introduced. Application of the fluorous tag in multistep synthesis of triaryl-substituted pyrimidine is also described. (C) 2005 Elsevier B.V. All rights reserved.
• A traceless perfluorooctylsulfonyl tag for deoxygenation of phenols under microwave irradiation
  作者：Wei Zhang、Tadamichi Nagashima、Yimin Lu、Christine Hiu-Tung Chen

  DOI：10.1016/j.tetlet.2004.04.115

  日期：2004.6

  The perfluorooctylsulfonyl group is introduced as a traceless tag for solution-phase palladium-catalyzed deoxygenation reactions. The synthetic efficiency is improved by microwave irradiation for reaction and fluorous solid-phase extraction for separation. Further application of this traceless tag for multistep synthesis of substituted hydantoin and pyrimidine is also described. (C) 2004 Elsevier Ltd. All rights reserved.
• A Highly Efficient Microwave-Assisted Suzuki Coupling Reaction of Aryl Perfluorooctylsulfonates with Boronic Acids
  作者：Wei Zhang、Christine Hiu-Tung Chen、Yimin Lu、Tadamichi Nagashima

  DOI：10.1021/ol0496428

  日期：2004.4.1

  strategy to improve the efficiency of Suzuki coupling reactions is introduced by combining fast microwave reaction with easy fluorous separation. Aryl perfluorooctylsulfonates derived from the corresponding phenols are coupled with aryl boronic acids to form biaryls under general microwave conditions. Both intermediates and products are purified by solid-phase extraction over FluoroFlash silica gel

  [反应：见正文]通过将快速微波反应与容易的荧光分离相结合，提出了一种提高铃木偶联反应效率的新策略。在常规微波条件下，将衍生自相应酚的芳基全氟辛基磺酸酯与芳基硼酸偶合形成联芳基。中间体和产物均通过在FluoroFlash硅胶上进行固相萃取来纯化。还描述了该标签策略在联芳基取代的乙内酰脲的多步合成中的应用。