3-[2-(2-bromopyridin-3-yl)ethyl]-N-methyl-N-phenylpyridine-2-carboxamide | 380614-72-2

• 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: 3-[2-(2-bromopyridin-3-yl)ethyl]-N-methyl-N-phenylpyridine-2-carboxamide
• CAS: 380614-72-2
• 化学式: C₂₀H₁₈BrN₃O
• 分子量: 396.286
• InChiKey: GKZFIAPOQDKGBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(2-bromopyridin-3-yl)ethyl]-N-methyl-N-phenylpyridine-2-carboxamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 以70.7%的产率得到4,15-Diazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-one
  参考文献：
  名称：

  An Anion-Induced Regio- and Chemoselective Acylation and Its Application to the Synthesis of an Anticancer Agent

  摘要：

  [GRAPHICS]An efficient Grignard- and organolithium-Induced regio- and chemoselective anionic acylation is reported. A number of tricyclic ketones are prepared in good to excellent yields via this method. This method is complementary to the Frieldel-Crafts acylation for elect ron-deficient substrates. A novel anisole-based Grignard reagent was developed to effect the cyclization of sterically hindered substrates. This novel reagent has been successfully applied to the synthesis of Sch 66336, a candidate for oncologic treatment.

  DOI：

  10.1021/ol016809d
• 作为产物：
  描述：

  3-methylpicolinanilide 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.83h， 生成 3-[2-(2-bromopyridin-3-yl)ethyl]-N-methyl-N-phenylpyridine-2-carboxamide
  参考文献：
  名称：

  An Anion-Induced Regio- and Chemoselective Acylation and Its Application to the Synthesis of an Anticancer Agent

  摘要：

  [GRAPHICS]An efficient Grignard- and organolithium-Induced regio- and chemoselective anionic acylation is reported. A number of tricyclic ketones are prepared in good to excellent yields via this method. This method is complementary to the Frieldel-Crafts acylation for elect ron-deficient substrates. A novel anisole-based Grignard reagent was developed to effect the cyclization of sterically hindered substrates. This novel reagent has been successfully applied to the synthesis of Sch 66336, a candidate for oncologic treatment.

  DOI：

  10.1021/ol016809d