2-(4-methyl-3-tosylphenyl)pyridine | 1350442-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-methyl-3-tosylphenyl)pyridine
• 英文别名: 2-[4-Methyl-3-(4-methylphenyl)sulfonylphenyl]pyridine；2-[4-methyl-3-(4-methylphenyl)sulfonylphenyl]pyridine
• CAS: 1350442-49-7
• 化学式: C₁₉H₁₇NO₂S
• 分子量: 323.415
• InChiKey: RSOFQYUFNSFDAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)吡啶 、 对甲苯磺酰氯 在 [RhCl2(p-cymene)]2 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以56%的产率得到2-(4-methyl-3-tosylphenyl)pyridine
  参考文献：
  名称：

  Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines

  摘要：

  A selective catalytic meta sulfonation of 2-phenylpyridines was found to occur in the presence of (arene)ruthenium(II) complexes upon reaction with sulfonyl chlorides. The 2-pyridyl group facilitates the formation of a stable Ru-C-aryl sigma bond that induces a strong para-directing effect. Electrophilic aromatic substitution proceeds with the sulfonyl chloride to furnish a sulfone at the position meta to the chelating group. This new catalytic process offers access to atypical regioselectivity for reactions involving chelation-assisted cyclometalation.

  DOI：

  10.1021/ja208286b

文献信息

• Ruthenium-Catalyzed Meta Sulfonation of 2-Phenylpyridines
  作者：Ourida Saidi、Jameel Marafie、Araminta E. W. Ledger、Po Man Liu、Mary F. Mahon、Gabriele Kociok-Köhn、Michael K. Whittlesey、Christopher G. Frost

  DOI：10.1021/ja208286b

  日期：2011.12.7

  A selective catalytic meta sulfonation of 2-phenylpyridines was found to occur in the presence of (arene)ruthenium(II) complexes upon reaction with sulfonyl chlorides. The 2-pyridyl group facilitates the formation of a stable Ru-C-aryl sigma bond that induces a strong para-directing effect. Electrophilic aromatic substitution proceeds with the sulfonyl chloride to furnish a sulfone at the position meta to the chelating group. This new catalytic process offers access to atypical regioselectivity for reactions involving chelation-assisted cyclometalation.