1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid 4-[(E)-3-(4-methoxy-phenyl)-3-oxo-propenyl]-phenyl ester | 731857-76-4

• 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 4-[(E)-3-(4-methoxy-phenyl)-3-oxo-propenyl]-phenyl ester
• 英文别名: [4-[(E)-3-(4-methoxyphenyl)-3-oxoprop-1-enyl]phenyl] 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate
• CAS: 731857-76-4
• 化学式: C₂₄H₁₃F₁₇O₅S
• 分子量: 736.403
• InChiKey: ZKXNORRCSBTBHQ-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  22

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 4-[(E)-3-(4-methoxy-phenyl)-3-oxo-propenyl]-phenyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 甲酸 、 lithium carbonate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 水 、 丙酮 、 甲苯 为溶剂， 反应 26.33h， 生成 4-(4-methoxyphenyl)-2,6-diphenylpyrimidine
  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：

  diethyl 2-(4-methoxyphenyl)-2-oxoethylphosphonate 、 4-formylphenyl perfluoro-1-1-octanesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以71%的产率得到1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluoro-octane-1-sulfonic acid 4-[(E)-3-(4-methoxy-phenyl)-3-oxo-propenyl]-phenyl ester
  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

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.