4-(pyrimidin-2-yl)phenyl 4-methylbenzenesulfonate | 1224437-52-8

• 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: 4-(pyrimidin-2-yl)phenyl 4-methylbenzenesulfonate
• 英文别名: (4-Pyrimidin-2-ylphenyl) 4-methylbenzenesulfonate；(4-pyrimidin-2-ylphenyl) 4-methylbenzenesulfonate
• CAS: 1224437-52-8
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: GWOJKHKNZSMWAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(pyrimidin-2-yl)phenyl 4-methylbenzenesulfonate 在 2-(2'-pyrimidyl)phenylpalladium(II) acetate 、 copper(II) trifluoroacetate 、 calcium chloride 作用下， 以 溶剂黄146 为溶剂， 反应 28.0h， 以86%的产率得到3,5-dichloro-4-(pyrimidin-2-yl)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Direct synthesis of ortho-dihalogenated arylpyrimidines using calcium halides as halogen sources

  摘要：

  Pyrimidines and their derivatives have been used as important motifs in materials and medicinal chemistry. In this Letter, a wide variety of ortho-dihalogenated arylpyrimidines were synthesized with high yields and functional-group tolerance using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air. The generated dichlorinated products could be further manipulated by stepwise Suzuki-Miyaura reaction to afford a wide range of ortho-functionalized arylpyrimidines amenable to physical and biological evaluations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.061
• 作为产物：
  描述：

  对甲苯磺酰氯 、 4-(pyrimidin-2-yl)phenol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以91%的产率得到4-(pyrimidin-2-yl)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  钯催化的芳基嘧啶的区域选择性 CH 键邻乙酰氧基化

  摘要：

  通过使用三氟乙酸铜作为助催化剂，开发了一种有效且具有区域选择性的钯催化的邻 CH 乙酰氧基化反应，以良好至极好的产率提供邻位单乙酰氧基化芳基嘧啶。制备了多种具有高区域选择性和官能团耐受性的氧化芳基嘧啶。

  DOI：

  10.1002/ejoc.201000631

文献信息

• Palladium-Catalyzed Monoselective Halogenation of CH Bonds: Efficient Access to Halogenated Arylpyrimidines using Calcium Halides
  作者：Bingrui Song、Xiaojian Zheng、Jun Mo、Bin Xu

  DOI：10.1002/adsc.200900778

  日期：2010.2.15

  A wide variety of ortho-halogenated arylpyrimidines were prepared with high monoselectivity and functional-group tolerance by using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air.

  通过在空气中使用卤化钙作为关键的卤化剂和三氟乙酸铜作为氧化剂，制备了具有高单选择性和官能团耐受性的多种邻卤代芳基嘧啶。
• Rhodium-Catalyzed Direct C–H Bond Cyanation of Arenes with Isocyanide
  作者：Xiaohu Hong、Hao Wang、Guangyin Qian、Qitao Tan、Bin Xu

  DOI：10.1021/jo500087g

  日期：2014.4.4

  An efficient rhodium-catalyzed regioselective C-H bond cyanation of arenes was developed using tert-butyl isocyanide as the cyanide source. A wide range of (hetero)aryl and cycloalkenyl nitriles could be afforded with high regioselectivity and good functional group tolerance.
• Palladium-Catalyzed Regioselective C-H Bond ortho-Acetoxylation of Arylpyrimidines
  作者：Xiaojian Zheng、Bingrui Song、Bin Xu

  DOI：10.1002/ejoc.201000631

  日期：——

  An efficient and regioselective palladium-catalyzed ortho C-H acetoxylation reaction was developed to afford ortho monoacetoxylated arylpyrimidines in good to excellent yields by using cupric trifluoroacetate as a cocatalyst. A wide variety of oxygenated arylpyrimidines were prepared with high regioselectivity and functional group tolerance.

  通过使用三氟乙酸铜作为助催化剂，开发了一种有效且具有区域选择性的钯催化的邻 CH 乙酰氧基化反应，以良好至极好的产率提供邻位单乙酰氧基化芳基嘧啶。制备了多种具有高区域选择性和官能团耐受性的氧化芳基嘧啶。
• Direct synthesis of ortho-dihalogenated arylpyrimidines using calcium halides as halogen sources
  作者：Xiaojian Zheng、Bingrui Song、Guifei Li、Bingxin Liu、Hongmei Deng、Bin Xu

  DOI：10.1016/j.tetlet.2010.10.061

  日期：2010.12

  Pyrimidines and their derivatives have been used as important motifs in materials and medicinal chemistry. In this Letter, a wide variety of ortho-dihalogenated arylpyrimidines were synthesized with high yields and functional-group tolerance using calcium halides as crucial halogenating agents and cupric trifluoroacetate as oxidant in the presence of air. The generated dichlorinated products could be further manipulated by stepwise Suzuki-Miyaura reaction to afford a wide range of ortho-functionalized arylpyrimidines amenable to physical and biological evaluations. (C) 2010 Elsevier Ltd. All rights reserved.