4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol | 945933-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol
• 英文别名: 4-nitro-6-[[(2'-(pyridin-2-yl)ethyl)methylamino]methyl]phenol
• CAS: 945933-77-7
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: XKWRXGNNYZQJKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.5
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol 、 [RuCl2(benzene)]2 、 ammonium hexafluorophosphate 在 triethylamine 作用下， 以 甲醇 为溶剂， 以57%的产率得到(η6-C6H6)Ru(4-nitro-6-[[(2'-(pyridin-2-yl)ethyl)methylamino]methyl]phenolate)PF6
  参考文献：
  名称：

  Half-sandwich η6-benzene Ru(II) complexes of phenolate-based pyridylalkylamine/alkylamine ligands: Synthesis, structure, and stabilization of one-electron oxidized species

  摘要：

  Four half-sandwich ruthenium(II) complexes [(eta(6)-C6H6)Ru(L-1-O)][PF6] (1), [(eta(6)-C6H6)Ru(L-2-O)][PF6] (2), [(eta(6)-C6H6)Ru(L-3-O)][PF6] (3), [(eta(6)-C6H6)Ru(L-4-O)][PF6] (4a), and [(eta(6)-C6H6)Ru(L-4-O)][BPh4] (4b) [L-1-OH, 4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-2-OH, 2,4-di-tert-butyl-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-3-OH, 2,4-di-tert-butyl-6-{[2'-((pyridin-2-yl)benzylamino)methyl}-phenol; L-4-OH, 2,4-di-tert-butyl-6-{[(2'-imethylaminoethyl)methylamino]methyl}-phenol (L-4-OH)], supported by a systematically varied series of tridentate phenolate-based pyridylalkylamine and alkylamine ligands are reported. The molecular structures of 1-3, 4a, and 4b have been elucidated in solution using H-1 NMR spectroscopy and of 1, 3, and 4b in the solid state by X-ray crystallography. Notably, due to coordination by the ligands the Ru center assumes a chiral center and in turn the central amine nitrogen also becomes chiral. The H-1 NMR spectra exhibit only one set of signals, suggesting that the reaction is completely diastereoselective [1: S-Ru,S-N/R-Ru,R-N; 2: R-Ru,R-N/S-Ru,S-N; 3: S-Ru,R-N/R-Ru,S-N; 4b: S-Ru,R-N/R-Ru,S-N]. The crystal packing in 1 and 3 is stabilized by C-H(center dot center dot center dot)0 interactions, in 4b no meaningful secondary interactions are observed. From the standpoint of generating phenoxyl radical, as investigated by cyclic voltammetry (CV), complex 1 is redox-inactive in MeCN solution. However, 2, 3, and 4a generate a one-electron oxidized phenoxyl radical coordinated species [2](2+center dot), [3](2+center dot), and [4a](2+center dot), respectively. The radical species are characterized by CV, UV-Vis, and EPR spectroscopy. The stability of the radical species has been determined by measuring the decay constant (UV-Vis spectroscopy). (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.03.041
• 作为产物：
  描述：

  2-(2-甲基氨基乙基)吡啶 、 2-氯甲基-4-硝基苯酚 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以70%的产率得到4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol
  参考文献：
  名称：

  Half-sandwich η6-benzene Ru(II) complexes of phenolate-based pyridylalkylamine/alkylamine ligands: Synthesis, structure, and stabilization of one-electron oxidized species

  摘要：

  Four half-sandwich ruthenium(II) complexes [(eta(6)-C6H6)Ru(L-1-O)][PF6] (1), [(eta(6)-C6H6)Ru(L-2-O)][PF6] (2), [(eta(6)-C6H6)Ru(L-3-O)][PF6] (3), [(eta(6)-C6H6)Ru(L-4-O)][PF6] (4a), and [(eta(6)-C6H6)Ru(L-4-O)][BPh4] (4b) [L-1-OH, 4-nitro-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-2-OH, 2,4-di-tert-butyl-6-{[(2'-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L-3-OH, 2,4-di-tert-butyl-6-{[2'-((pyridin-2-yl)benzylamino)methyl}-phenol; L-4-OH, 2,4-di-tert-butyl-6-{[(2'-imethylaminoethyl)methylamino]methyl}-phenol (L-4-OH)], supported by a systematically varied series of tridentate phenolate-based pyridylalkylamine and alkylamine ligands are reported. The molecular structures of 1-3, 4a, and 4b have been elucidated in solution using H-1 NMR spectroscopy and of 1, 3, and 4b in the solid state by X-ray crystallography. Notably, due to coordination by the ligands the Ru center assumes a chiral center and in turn the central amine nitrogen also becomes chiral. The H-1 NMR spectra exhibit only one set of signals, suggesting that the reaction is completely diastereoselective [1: S-Ru,S-N/R-Ru,R-N; 2: R-Ru,R-N/S-Ru,S-N; 3: S-Ru,R-N/R-Ru,S-N; 4b: S-Ru,R-N/R-Ru,S-N]. The crystal packing in 1 and 3 is stabilized by C-H(center dot center dot center dot)0 interactions, in 4b no meaningful secondary interactions are observed. From the standpoint of generating phenoxyl radical, as investigated by cyclic voltammetry (CV), complex 1 is redox-inactive in MeCN solution. However, 2, 3, and 4a generate a one-electron oxidized phenoxyl radical coordinated species [2](2+center dot), [3](2+center dot), and [4a](2+center dot), respectively. The radical species are characterized by CV, UV-Vis, and EPR spectroscopy. The stability of the radical species has been determined by measuring the decay constant (UV-Vis spectroscopy). (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.03.041