N-(anthracen-9-yl)picolinamide | 1423074-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(anthracen-9-yl)picolinamide
• 英文别名: N-anthracen-9-ylpyridine-2-carboxamide
• CAS: 1423074-18-3
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: YUFCKKOXOSFDIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(anthracen-9-yl)picolinamide 、 sodium 4-methylbenzenesulfinate 在 copper diacetate 、 sodium acetate 、 manganese(III) triacetate dihydrate 作用下， 反应 1.5h， 以48%的产率得到pyridine-2-carboxylic acid[10-(toluene-4-sulfonyl)-anthracen-9-yl]amide
  参考文献：
  名称：

  铜催化的亚磺酸钠和亚磺酸锂对苯胺的苯胺远程官能化

  摘要：

  已开发出铜催化的苯胺与亚磺酸钠和亚硫酸锂的交叉脱氢偶联反应。通过使用以Mn（OAc）3作为化学计量助氧化剂的协同反应系统，苯胺的高度选择性对官能化得以实现。耐受各种官能团，并以高收率获得所需产物。该方法不仅为芳基砜的合成提供了一种新颖的方法，而且还可能为开发铜催化的对位选择性CH官能团提供新的机会。

  DOI：

  10.1002/chem.201605101
• 作为产物：
  描述：

  2-吡啶甲酸 、 9-氨基蒽 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以25%的产率得到N-(anthracen-9-yl)picolinamide
  参考文献：
  名称：

  Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System

  摘要：

  A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.

  DOI：

  10.1021/jo400017v

文献信息

• Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System
  作者：Lehao Huang、Qian Li、Chen Wang、Chenze Qi

  DOI：10.1021/jo400017v

  日期：2013.4.5

  A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.
• Copper-Catalyzed Remote <i>para</i> -C−H Functionalization of Anilines with Sodium and Lithium Sulfinates
  作者：Shuai Liang、Michael Bolte、Georg Manolikakes

  DOI：10.1002/chem.201605101

  日期：2017.1.1

  A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel

  已开发出铜催化的苯胺与亚磺酸钠和亚硫酸锂的交叉脱氢偶联反应。通过使用以Mn（OAc）3作为化学计量助氧化剂的协同反应系统，苯胺的高度选择性对官能化得以实现。耐受各种官能团，并以高收率获得所需产物。该方法不仅为芳基砜的合成提供了一种新颖的方法，而且还可能为开发铜催化的对位选择性CH官能团提供新的机会。