2-((4-methylbenzyl)sulfonyl)pyridine

• 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-((4-methylbenzyl)sulfonyl)pyridine
• 英文别名: 2-[(4-Methylphenyl)methylsulfonyl]pyridine
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: XQAVCJHXNRTNEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 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：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-碘吡啶 、 4-甲基苄溴 在 sodium dithionite 、 四丁基碘化铵 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 以83%的产率得到2-((4-methylbenzyl)sulfonyl)pyridine
  参考文献：
  名称：

  （杂）芳基碘化物与连二亚硫酸钠的无催化剂磺酰化

  摘要：

  市售廉价的连二亚硫酸钠被用作磺酰基的来源，用于在无催化剂的条件下从（杂）芳基碘化物合成砜和磺酰胺。在反应过程中，原位生成的亚磺酸钠是关键中间体，可以进一步转化为多种砜和磺酰胺。这种转变是通过连二亚硫酸钠引发的自由基过程而进行的，为获得含磺酰基化合物提供了便利的途径。

  DOI：

  10.1002/adsc.201801445

文献信息

• Catalyst-Free Sulfonylation of (Hetero)aryl Iodides with Sodium Dithionite
  作者：Yuewen Li、Tong Liu、Guanyinsheng Qiu、Jie Wu

  DOI：10.1002/adsc.201801445

  日期：2019.3.5

  The commercially available and cheap sodium dithionite is used as the source of sulfonyl group for the synthesis of sulfones and sulfonamides from (hetero)aryl iodides under catalyst‐free conditions. During the reaction process, sodium sulfinates generated in situ are the key intermediate, which can be further converted into diverse sulfones and sulfonamides. This transformation proceeds through a

  市售廉价的连二亚硫酸钠被用作磺酰基的来源，用于在无催化剂的条件下从（杂）芳基碘化物合成砜和磺酰胺。在反应过程中，原位生成的亚磺酸钠是关键中间体，可以进一步转化为多种砜和磺酰胺。这种转变是通过连二亚硫酸钠引发的自由基过程而进行的，为获得含磺酰基化合物提供了便利的途径。
• Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce <i>Z</i>- and <i>E</i>-Monofluoroalkenes
  作者：Yanchuan Zhao、Fanzhou Jiang、Jinbo Hu

  DOI：10.1021/jacs.5b02112

  日期：2015.4.22

  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.