(2,6-Difluoropyridin-3-yl)-(2-methoxyphenyl)methanone | 1158955-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,6-Difluoropyridin-3-yl)-(2-methoxyphenyl)methanone
• CAS: 1158955-24-8
• 化学式: C₁₃H₉F₂NO₂
• 分子量: 249.217
• InChiKey: APNVCBUDTQRKHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,6-Difluoropyridin-3-yl)-(2-methoxyphenyl)methanone 、 叔丁胺 在 一水合肼 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以75%的产率得到C₁₇H₂₀N₄O
  参考文献：
  名称：

  An efficient access to 3,6-disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reaction and pyrazole formation

  摘要：

  A general and efficient synthetic method for the synthesis of biologically important series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines was discovered. 2,6-Difluoropyridine was deprotonated using 1.1 equiv of n-BuLi in THF at <-60 degrees C, followed by quenching with a variety of Weinreb amides to generate 2,6-Difluoro-3-ketopyridines in high yields. A mild tandem reaction sequence of selective nucleophilic Substitution of the 6-fluoride with a variety of nucleophiles, followed by hydrazine substitution of the 2-fluoride and pyrazole formation in a one-pot fashion afforded a series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines in moderate to good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.142
• 作为产物：
  描述：

  2,6-二氟吡啶 、 2,N-二甲氧基-N-甲基苯甲酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以93%的产率得到(2,6-Difluoropyridin-3-yl)-(2-methoxyphenyl)methanone
  参考文献：
  名称：

  An efficient access to 3,6-disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reaction and pyrazole formation

  摘要：

  A general and efficient synthetic method for the synthesis of biologically important series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines was discovered. 2,6-Difluoropyridine was deprotonated using 1.1 equiv of n-BuLi in THF at <-60 degrees C, followed by quenching with a variety of Weinreb amides to generate 2,6-Difluoro-3-ketopyridines in high yields. A mild tandem reaction sequence of selective nucleophilic Substitution of the 6-fluoride with a variety of nucleophiles, followed by hydrazine substitution of the 2-fluoride and pyrazole formation in a one-pot fashion afforded a series of 3,6-disubstituted-1H-pyrazolo[3,4-b]pyridines in moderate to good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.142