4-methyl-N-[2-(trifluoromethyl)-2H-pyridin-1-yl]benzenesulfonamide | 1385096-44-5

• 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-methyl-N-[2-(trifluoromethyl)-2H-pyridin-1-yl]benzenesulfonamide
• CAS: 1385096-44-5
• 化学式: C₁₃H₁₃F₃N₂O₂S
• 分子量: 318.32
• InChiKey: CTIAYAFVCOEBIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methyl-N-[2-(trifluoromethyl)-2H-pyridin-1-yl]benzenesulfonamide 在 sodium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 diethyl 7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyridinedicarboxylate

  摘要：

  Two syntheses of 7-trifluoromethylpyrazolo[1,5-a]pyridine dicarboxylate have been described. Approach A utilizes a nucleophilic addition of a trifluoromethyl group to N-p-toluenesulfonyliminopyridinium ylide followed by aromatization and subsequent cycloaddition with diethyl acetylenedicarboxylate to give 1b in modest yield. Approach B involves a selective zincation of pyrazolopyridine dicarboxylate at the C-7 position with (TMP)(2)Zn center dot 2LiCl.2MgCl(2) followed by iodination and trifluoromethylation to give 1b in good yield. The process in approach B has been successfully demonstrated on scale. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.136
• 作为产物：
  描述：

  对甲苯磺酰氯 在 cesium fluoride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-methyl-N-[2-(trifluoromethyl)-2H-pyridin-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyridinedicarboxylate

  摘要：

  Two syntheses of 7-trifluoromethylpyrazolo[1,5-a]pyridine dicarboxylate have been described. Approach A utilizes a nucleophilic addition of a trifluoromethyl group to N-p-toluenesulfonyliminopyridinium ylide followed by aromatization and subsequent cycloaddition with diethyl acetylenedicarboxylate to give 1b in modest yield. Approach B involves a selective zincation of pyrazolopyridine dicarboxylate at the C-7 position with (TMP)(2)Zn center dot 2LiCl.2MgCl(2) followed by iodination and trifluoromethylation to give 1b in good yield. The process in approach B has been successfully demonstrated on scale. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.136

文献信息

• Synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyridinedicarboxylate
  作者：Pek Chong、Roman Davis、Vassil Elitzin、Mark Hatcher、Bing Liu、Matthew Salmons、Elie Tabet

  DOI：10.1016/j.tetlet.2012.09.136

  日期：2012.12

  Two syntheses of 7-trifluoromethylpyrazolo[1,5-a]pyridine dicarboxylate have been described. Approach A utilizes a nucleophilic addition of a trifluoromethyl group to N-p-toluenesulfonyliminopyridinium ylide followed by aromatization and subsequent cycloaddition with diethyl acetylenedicarboxylate to give 1b in modest yield. Approach B involves a selective zincation of pyrazolopyridine dicarboxylate at the C-7 position with (TMP)(2)Zn center dot 2LiCl.2MgCl(2) followed by iodination and trifluoromethylation to give 1b in good yield. The process in approach B has been successfully demonstrated on scale. (C) 2012 Elsevier Ltd. All rights reserved.