1-(p-tolyl)imidazo[1,5-a]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(p-tolyl)imidazo[1,5-a]pyridine
• 英文别名: 1-(4-Methylphenyl)imidazo[1,5-a]pyridine
• 化学式: C₁₄H₁₂N₂
• 分子量: 208.263
• InChiKey: ATCJXIPRZFDSNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-辛炔 、 1-(p-tolyl)imidazo[1,5-a]pyridine 在 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到(E)-3-(oct-4-en-4-yl)-1-(p-tolyl)imidazo[1,5-a]pyridine
  参考文献：
  名称：

  Controlled Regiodivergent C–H Bond Activation of Imidazo[1,5-a]pyridine via Synergistic Cooperation between Aluminum and Nickel

  摘要：

  The catalytic method features a cooperative interaction between Ni and Al imparting remote C-H alkenylation at the C5 position of imidazo[1,5-a]pyridine with alkynes at mild conditions. Exclusion of AlMe3 switches the selectivity to the C3 position. Reactions with styrene and other olefinic substrates affording C5-adducts by Ni/Al catalysis are also included.

  DOI：

  10.1021/ol502314p
• 作为产物：
  描述：

  1-溴-咪唑并[1,5-a]吡啶 、 4-甲苯硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以89%的产率得到1-(p-tolyl)imidazo[1,5-a]pyridine
  参考文献：
  名称：

  Controlled Regiodivergent C–H Bond Activation of Imidazo[1,5-a]pyridine via Synergistic Cooperation between Aluminum and Nickel

  摘要：

  The catalytic method features a cooperative interaction between Ni and Al imparting remote C-H alkenylation at the C5 position of imidazo[1,5-a]pyridine with alkynes at mild conditions. Exclusion of AlMe3 switches the selectivity to the C3 position. Reactions with styrene and other olefinic substrates affording C5-adducts by Ni/Al catalysis are also included.

  DOI：

  10.1021/ol502314p

文献信息

• US7714319B2
  申请人：——

  公开号：US7714319B2

  公开（公告）日：2010-05-11
• Controlled Regiodivergent C–H Bond Activation of Imidazo[1,5-<i>a</i>]pyridine via Synergistic Cooperation between Aluminum and Nickel
  作者：Ming-Shiuan Yu、Wei-Chih Lee、Chih-Hao Chen、Fu-Yu Tsai、Tiow-Gan Ong

  DOI：10.1021/ol502314p

  日期：2014.9.19

  The catalytic method features a cooperative interaction between Ni and Al imparting remote C-H alkenylation at the C5 position of imidazo[1,5-a]pyridine with alkynes at mild conditions. Exclusion of AlMe3 switches the selectivity to the C3 position. Reactions with styrene and other olefinic substrates affording C5-adducts by Ni/Al catalysis are also included.