2-(pyrid-2′-yl)acridine | 857613-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(pyrid-2′-yl)acridine
• 英文别名: 2-(pyridin-2-yl)acridine；pad；2-Pyridin-2-ylacridine；2-pyridin-2-ylacridine
• CAS: 857613-73-1
• 化学式: C₁₈H₁₂N₂
• 分子量: 256.307
• InChiKey: SKFOLFVGNLNUCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 sodium hexaflorophosphate 、 2-(pyrid-2′-yl)acridine 在 NaOH 作用下， 以 乙腈 为溶剂， 生成 [Ru(2-(pyridin-2-yl)acridine(-1H))(acetonitrile)4]PF6
  参考文献：
  名称：

  Proton-Induced Dynamic Equilibrium between Cyclometalated Ruthenium rNHC (Remote N-Heterocyclic Carbene) Tautomers with an NAD⁺/NADH Function

  摘要：

  Cyclometalated ruthenium(II) complexes having acridine moieties have been synthesized and characterized by spectroscopic methods. Protonation of the acridine nitrogen of the ruthenium(II) complexes not only causes dynamic equilibrium with remote N-heterocyclic carbene Ru=C complexes but also generates the NAD(+)-/NADH redox function driven by a proton-coupled two-electron transfer accompanying a reversible C-H bond formation in the pyridinium ring.

  DOI：

  10.1021/ic200315f
• 作为产物：
  描述：

  2-(pyridin-2-yl)-1,2,3,4-tetrahydroacridine 在 10% palladium on activated charcoal 作用下， 以 4-异丙基甲苯 为溶剂， 反应 24.0h， 生成 2-(pyrid-2′-yl)acridine 、 2-(pyridin-2-yl)-9,10-dihydroacridine
  参考文献：
  名称：

  Proton-Induced Dynamic Equilibrium between Cyclometalated Ruthenium rNHC (Remote N-Heterocyclic Carbene) Tautomers with an NAD⁺/NADH Function

  摘要：

  Cyclometalated ruthenium(II) complexes having acridine moieties have been synthesized and characterized by spectroscopic methods. Protonation of the acridine nitrogen of the ruthenium(II) complexes not only causes dynamic equilibrium with remote N-heterocyclic carbene Ru=C complexes but also generates the NAD(+)-/NADH redox function driven by a proton-coupled two-electron transfer accompanying a reversible C-H bond formation in the pyridinium ring.

  DOI：

  10.1021/ic200315f

文献信息

• Follow-Up Study of <i>Trans</i>-C to <i>Cis</i>-C Thermally or Photochemically Induced Isomerization of Terpyridine Adducts of Cycloruthenated 2-Aryl-2′-pyridine Compounds
  作者：Moussa Ali、Yann Cornaton、Jean-Pierre Djukic、Michel Pfeffer

  DOI：10.1021/acs.inorgchem.3c03671

  日期：2024.3.18

  reaction between [Ru(3-acridine-2′-C5H4N-κC,N) (MeCN)4]PF6, 4, and terpy in MeOH/MeCN at 60 °C for 24 h. Similar to 2, the isomerization of 6 to [Ru(3-acridine-2′-C5H4N-κC,N)(MeCN-trans-C) (terpy)]PF6, 7, could be induced thermally (48 h at 60 °C in pure MeOH) or photochemically under UV radiation in MeCN at room temperature. A compound closely related to 7 but in which MeCN was replaced by H2O was

  已知2-苯基,吡啶 ( phpy ) 衍生物 [Ru( phpy -κC,N) (MeCN -trans- N)( terpy )]PF 6 , 2异构化为 [Ru( phpy -κC,N) 的机理)(MeCN -trans- C)( terpy )]PF 6 ( terpy = 2,2′;6′,2″-三联吡啶), 3 , 在温度 >50 °C 下已通过1 H NMR 光谱和DFT 计算。室温下 20 小时后，MeCN 中也可定量发生由紫外光引起的2至3的光异构化。对于相关化合物 [Ru(3-acridine-2'-C 5 H 4 N-κC,N)(MeCN -trans- N)(2,2';6', 2″-三联吡啶)]PF 6 , 6 (吖啶=二苯并[ b , e ]吡啶或2,3-苯并喹啉)，由[Ru(3-吖啶-2'-C 5 H 4 N)之间的反应获得-κC,N) (MeCN) 4 ]PF 6
• Proton-Induced Dynamic Equilibrium between Cyclometalated Ruthenium rNHC (Remote N-Heterocyclic Carbene) Tautomers with an NAD⁺/NADH Function
  作者：Sumanta Kumar Padhi、Katsuaki Kobayashi、Shinya Masuno、Koji Tanaka

  DOI：10.1021/ic200315f

  日期：2011.6.20

  Cyclometalated ruthenium(II) complexes having acridine moieties have been synthesized and characterized by spectroscopic methods. Protonation of the acridine nitrogen of the ruthenium(II) complexes not only causes dynamic equilibrium with remote N-heterocyclic carbene Ru=C complexes but also generates the NAD(+)-/NADH redox function driven by a proton-coupled two-electron transfer accompanying a reversible C-H bond formation in the pyridinium ring.