3-(4-phenylpiperazin-1-yl)-6-(para-tolyl)pyridazine | 1417455-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-phenylpiperazin-1-yl)-6-(para-tolyl)pyridazine
• 英文别名: 3-(4-Methylphenyl)-6-(4-phenylpiperazin-1-yl)pyridazine；3-(4-methylphenyl)-6-(4-phenylpiperazin-1-yl)pyridazine
• CAS: 1417455-16-3
• 化学式: C₂₁H₂₂N₄
• 分子量: 330.432
• InChiKey: PWHWSYYIYGGSCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-苯基哌嗪 在 bis(bipyridine)nickel(II) bromide 、 四丁基溴化铵 、 三乙胺 作用下， 以 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-(4-phenylpiperazin-1-yl)-6-(para-tolyl)pyridazine
  参考文献：
  名称：

  An Electrochemical Nickel-Catalyzed Arylation of 3-Amino-6-Chloropyridazines

  摘要：

  3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.

  DOI：

  10.1021/jo3022428

文献信息

• Synthesis and biological evaluation of 3-amino-, 3-alkoxy- and 3-aryloxy-6-(hetero)arylpyridazines as potent antitumor agents
  作者：Stéphane Sengmany、Mathilde Sitter、Eric Léonel、Erwan Le Gall、Gervaise Loirand、Thierry Martens、Didier Dubreuil、Florian Dilasser、Morgane Rousselle、Vincent Sauzeau、Jacques Lebreton、Muriel Pipelier、Rémy Le Guével

  DOI：10.1016/j.bmcl.2018.12.050

  日期：2019.3

  Various 3-amino-, 3-aryloxy- and alkoxy-6-arylpyridazines have been synthesized by an electrochemical reductive cross-coupling between 3-amino-, 3-aryloxy- or 3-alkoxy-6-chloropyridazines and aryl or heteroaryl halides. In vitro antiproliferative activity of these products was evaluated against a representative panel of cancer cell lines (HuH7, CaCo-2, MDA-MB-231, HCT116, PC3, NCI-H727, HaCaT) and

  通过3-氨基-，3-芳氧基-或3-烷氧基-6-氯哒嗪与芳基或杂芳基卤化物之间的电化学还原交叉偶联，已经合成了各种3-氨基-，3-芳氧基-和烷氧基-6-芳基哒嗪。评估了这些产品对代表性癌细胞系（HuH7，CaCo-2，MDA-MB-231，HCT116，PC3，NCI-H727，HaCaT）的体外抗增殖活性，并强调了更有效衍生物的致癌性预防在建立人类乳腺癌细胞系MDA-MB 468-Luc与p44 / 42和Akt依赖性信号传导途径的相互作用之前，已对MDA-MB 468-Luc进行了研究。
• An Electrochemical Nickel-Catalyzed Arylation of 3-Amino-6-Chloropyridazines
  作者：Stéphane Sengmany、Arnaud Vitu-Thiebaud、Erwan Le Gall、Sylvie Condon、Eric Léonel、Christine Thobie-Gautier、Muriel Pipelier、Jacques Lebreton、Didier Dubreuil

  DOI：10.1021/jo3022428

  日期：2013.1.18

  3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.