7-methoxy-N,5-bis(4-methoxyphenyl)-3-(4-methoxyphenylimino)-3,5-dihydrophenazin-2-amine | 306970-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-methoxy-N,5-bis(4-methoxyphenyl)-3-(4-methoxyphenylimino)-3,5-dihydrophenazin-2-amine
• 英文别名: 6-p-anisyl-2-(p-anisylamino)-3(4H)-p-anisylimine-9-methoxyphenazine；7-methoxy-N,5-bis(4-methoxyphenyl)-3-(4-methoxyphenyl)iminophenazin-2-amine
• CAS: 306970-26-3
• 化学式: C₃₄H₃₀N₄O₄
• 分子量: 558.637
• InChiKey: HXXQMBADNNXIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Os(2-(m-tolylazo)-pyridine)2Br2 、 7-methoxy-N,5-bis(4-methoxyphenyl)-3-(4-methoxyphenylimino)-3,5-dihydrophenazin-2-amine 在 sodium carbonate 作用下， 以 乙二醇甲醚 为溶剂， 以80%的产率得到6-p-anisyl-2-(p-anisylamino)-3[(4H)-p-anisyliminobis(2-(m-tolylazo)pyridine)]-9-methoxyphenazineosmium(II) bromide
  参考文献：
  名称：

  Ferric-Chloride-Promoted Oxidation of p-Anisidine to an N-Substituted Phenazine Derivative − Structural Elucidation, Protic Equilibria and Coordination Chemistry of the Phenazine

  摘要：

  DOI：

  10.1002/1099-0682(200009)2000:9<1961::aid-ejic1961>3.3.co;2-2
• 作为产物：
  描述：

  甲氧苯胺 在 高氯酸 、 氧气 作用下， 以30%的产率得到7-methoxy-N,5-bis(4-methoxyphenyl)-3-(4-methoxyphenylimino)-3,5-dihydrophenazin-2-amine
  参考文献：
  名称：

  Aerial Oxidation of Protonated Aromatic Amines. Isolation, X-ray Structure, and Redox and Spectral Characteristics of N- Containing Dyes

  摘要：

  This work reports the results of our investigation on the aerial oxidation of aromatic amines that are promoted by protic acid. While primary aromatic amines produce substituted phenazines as major products, N-phenyl-o-phenylenediamine produces polycyclic aromatic heterocycles like azaacene and secondary and tertiary amines give exclusively the dyes containing a triphenylmethane moiety. Isolation of the compounds and the effects of substitutions on the aromatic rings have been investigated. In this context, plausible reaction steps that are involved have been discussed. Single-crystal X-ray structure analyses of the representative compounds are solved to authenticate their formation. In almost every case, a high degree of delocalization of electron was noted. The compounds have been characterized thoroughly and show rich spectral properties. For example, the phenazine molecules exhibited absorption peaks between 475 and 605 nm because of the charge-transfer transition from the amine and tricyclopyrazine moiety. Their acidochromic and solvatochromic behaviors, which are supported by theoretical calculations, are investigated. The polycyclic azacene molecule exhibits strong absorption in the visible region and fluoresces with high quantum yield. The phenazine dyes undergo a quasi-reversible reduction at a low cathodic potential that varies linearly as a function of Hammett's constant.

  DOI：

  10.1021/jo3019126

文献信息

• Two Novel Reactions of a Ruthenium‐Coordinated Phenazine – Oxidative Aromatic Ring Hydroxylation and Dimerization via a New C–N Bond Formation
  作者：Priyabrata Banerjee、Golam Mostafa、Alfonso Castiñeiras、Sreebrata Goswami

  DOI：10.1002/ejic.200600864

  日期：2007.1

  CF3SO3–). The complexes 3 and 4 were also obtained from the pure complex 2 under two different experimental conditions. Oxidative aromatic ring hydroxylation of the complex 2 produced 3 while the diruthenium complex, 4, was formed by dimerization of 2 via a new C–N bond formation. The products were thoroughly characterized with the help of 1H NMR and ESI-MS spectral measurements. Final authentication

  [Ru(CH3OH)2(N∧N)2]2+ [N∧N = 2,2'-联吡啶 (bpy) 和 1,10-邻菲咯啉(phen)] 与吩嗪配体的反应，[ HL1 = 6-p-anisyl-2-(p-anisylamino)-3(4H)-p-anisylimine-9-methoxyphenazine] 在碱 (NEt3) 存在下得到两个单核钌配合物，[Ru(L1)( N∧N)2]X(2)，和[Ru(LO)(N∧N)2]X2(3)，[LO = 7-甲氧基-5-(4-甲氧基苯基)-2,3-双( 4-甲氧基苯基亚氨基)-3,5-二氢-2H-吩嗪-1-one]与二钌络合物[(N∧N)2RuL2Ru(N∧N)2]X3 (4), [L2 = 7,8' -二甲氧基-5,10'-双(4-甲氧基苯基)-2,3'-双(4-甲氧基苯基氨基)-3,2'-双(4'-甲氧基苯基亚氨基)-3,5,2',10'-四氢-[1,5'
• Ferric-Chloride-Promoted Oxidation of p-Anisidine to an N-Substituted Phenazine Derivative − Structural Elucidation, Protic Equilibria and Coordination Chemistry of the Phenazine
  作者：Amit??K. Ghosh、Kedar??N. Mitra、Golam Mostafa、Sreebrata Goswami

  DOI：10.1002/1099-0682(200009)2000:9<1961::aid-ejic1961>3.3.co;2-2

  日期：2000.9
• Aerial Oxidation of Protonated Aromatic Amines. Isolation, X-ray Structure, and Redox and Spectral Characteristics of N- Containing Dyes
  作者：Suman K Roy、Subhas Samanta、Mominul Sinan、Pradip Ghosh、Sreebrata Goswami

  DOI：10.1021/jo3019126

  日期：2012.11.16

  This work reports the results of our investigation on the aerial oxidation of aromatic amines that are promoted by protic acid. While primary aromatic amines produce substituted phenazines as major products, N-phenyl-o-phenylenediamine produces polycyclic aromatic heterocycles like azaacene and secondary and tertiary amines give exclusively the dyes containing a triphenylmethane moiety. Isolation of the compounds and the effects of substitutions on the aromatic rings have been investigated. In this context, plausible reaction steps that are involved have been discussed. Single-crystal X-ray structure analyses of the representative compounds are solved to authenticate their formation. In almost every case, a high degree of delocalization of electron was noted. The compounds have been characterized thoroughly and show rich spectral properties. For example, the phenazine molecules exhibited absorption peaks between 475 and 605 nm because of the charge-transfer transition from the amine and tricyclopyrazine moiety. Their acidochromic and solvatochromic behaviors, which are supported by theoretical calculations, are investigated. The polycyclic azacene molecule exhibits strong absorption in the visible region and fluoresces with high quantum yield. The phenazine dyes undergo a quasi-reversible reduction at a low cathodic potential that varies linearly as a function of Hammett's constant.