2-((fluoro(p-tolyl)methyl)sulfonyl)pyridine | 1426892-09-2

• 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: 2-((fluoro(p-tolyl)methyl)sulfonyl)pyridine
• 英文别名: 2-[Fluoro-(4-methylphenyl)methyl]sulfonylpyridine
• CAS: 1426892-09-2
• 化学式: C₁₃H₁₂FNO₂S
• 分子量: 265.308
• InChiKey: FKLQOGAEDUOPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((fluoro(p-tolyl)methyl)sulfonyl)pyridine 在 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (E)-2-(2-fluoro-2-(p-tolyl)vinyl)naphthalene
  参考文献：
  名称：

  Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes

  摘要：

  The monofluoroalkene motif is important in drug development as it serves as a peptide bond isostere and is found in a number of biologically active compounds with various pharmacological activities. Direct olefination of carbonyl compound is a straightforward way to prepare monofluoroalkenes; however, these methods often result in a mixture of Z- and E-isomers that cannot be easily separated. We discovered a unique spontaneous resolving reaction that simultaneously addresses the problems in the synthesis and separation of Z- and E-monofluoroalkenes. The reaction is accompanied by a highly efficient spontaneous kinetic resolution and phase labeling of monofluoroalkene precursors which allows the separation of Z- and E-monofluoroalkenes by liquid-liquid extraction. The application of the method is demonstrated by the synthesis and separation of potential anticancer agents, which are inseparable by HPLC.

  DOI：

  10.1021/jacs.5b02112
• 作为产物：
  描述：

  2-((4-methylbenzyl)sulfonyl)pyridine 在 zinc(II) chloride 、 lithium hexamethyldisilazane 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以76%的产率得到2-((fluoro(p-tolyl)methyl)sulfonyl)pyridine
  参考文献：
  名称：

  Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce Z- and E-Monofluoroalkenes

  摘要：

  The monofluoroalkene motif is important in drug development as it serves as a peptide bond isostere and is found in a number of biologically active compounds with various pharmacological activities. Direct olefination of carbonyl compound is a straightforward way to prepare monofluoroalkenes; however, these methods often result in a mixture of Z- and E-isomers that cannot be easily separated. We discovered a unique spontaneous resolving reaction that simultaneously addresses the problems in the synthesis and separation of Z- and E-monofluoroalkenes. The reaction is accompanied by a highly efficient spontaneous kinetic resolution and phase labeling of monofluoroalkene precursors which allows the separation of Z- and E-monofluoroalkenes by liquid-liquid extraction. The application of the method is demonstrated by the synthesis and separation of potential anticancer agents, which are inseparable by HPLC.

  DOI：

  10.1021/jacs.5b02112

文献信息

• 一种制备高选择性单氟烯烃的试剂
  申请人：中国科学院上海有机化学研究所

  公开号：CN104447521B

  公开（公告）日：2021-09-03

  本发明提供了一种制备高选择性单氟烯烃的试剂，具体地，本发明提供了一种能够高选择性地制备单氟烯烃的试剂，及使用所述试剂制备单氟烯烃的方法。本发明的方法条件温和，转化率高，可以任选地用于制备高度构型纯的Z式或E式烯烃，成本低，适合用于大规模生产。
• Copper-Catalyzed Debenzoylative Monofluoromethylation of Aryl Iodides Assisted by the Removable (2-Pyridyl)sulfonyl Group
  作者：Yanchuan Zhao、Chuanfa Ni、Fanzhou Jiang、Bing Gao、Xiao Shen、Jinbo Hu

  DOI：10.1021/cs4000574

  日期：2013.4.5

  A new method for aromatic monofluoromethylation was developed. Aryl iodides can be efficiently transformed into the corresponding monofluoromethylated products by a copper-catalyzed debenzoylative fluoroalkylation with 2-PySO2CHFCOR and subsequent reductive desulfonylation. The (2-pyridyl)sulfonyl moiety plays an important role in the copper-catalyzed cross-coupling, and it can be removed easily through Bu3SnH-mediated desulfonylation.