2-amino-3,5-dihydro-5-phenyl-3-phenyliminophenazine | 3297-84-5

• 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: 2-amino-3,5-dihydro-5-phenyl-3-phenyliminophenazine
• 英文别名: 3,5-dihydro-5-phenyl-3-(phenylimino)phenazin-2-amine；2-Amino-3,5-dihydro-5-phenyl-3-phenyliminophenazin；5-phenyl-3-phenylimino-3,5-dihydro-phenazine-2-ylamine；(3-amino-10-phenyl-10H-phenazin-2-ylidene)-phenyl-amine；2-amino-3-anilino-5-phenyl-phenazinium betaine；2-Amino-3-anilino-5-phenyl-phenazinium-betain；phenz；5-Phenyl-3-phenyliminophenazin-2-amine
• CAS: 3297-84-5
• 化学式: C₂₄H₁₈N₄
• 分子量: 362.434
• InChiKey: USSJZKOFSRWJGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  257-259 °C
• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-amino-3,5-dihydro-5-phenyl-3-phenyliminophenazine 在 氯仿 、 溴 作用下， 生成 2-bromoamino-3-(4-bromo-anilino)-5-phenyl-phenazinium betaine
  参考文献：
  名称：

  Barry et al., Journal of the Chemical Society, 1959, p. 3217,3220,3222

  摘要：

  DOI：
• 作为产物：
  描述：

  3-amino-2,10-dihydro-4-iodo-10-phenyl-2-phenyliminophenazine 在 环己胺 作用下， 反应 6.0h， 以63%的产率得到2-amino-3,5-dihydro-5-phenyl-3-phenyliminophenazine
  参考文献：
  名称：

  一些新型卤代吩嗪衍生物

  摘要：

  3-氨基-10-芳基-2-芳基-2,10-二氢吩嗪1在吩嗪核的4位发生碘化反应，生成的化合物与通过用钠氧化适当的N-芳基-邻-苯二胺所获得的化合物相同酸存在下的碘酸盐。溴化也发生在该位置，但是第二个溴原子进入芳基氨基部分的对位。异构体10-芳基-3-芳基-氨基-2,10-二氢-2-亚氨基吩嗪2生成不稳定的碘代衍生物，但在吩嗪核的1位和4位以及邻位和对位溴化芳基氨基取代基的-位。初步的氯化实验表明，取代模式与为溴化产物建立的类似。还记录了通过与伯胺或仲胺反应从吩嗪环中除去溴和碘，并记录了它们被氢而不是胺残基取代的情况。

  DOI：

  10.1002/jhet.5570230262

文献信息

• Oxidative <i>ortho</i>-C-N Fusion of Aniline by OsO₄. Isolation, Characterization of Oxo-Amido Osmium(VI) Complexes, and their Catalytic Activities for Oxidative C−C Bond Cleavage of Unsaturated Hydrocarbons
  作者：Subhas Samanta、Laksmikanta Adak、Ranjan Jana、Golam Mostafa、Heikki M. Tuononen、Brindaban C. Ranu、Sreebrata Goswami

  DOI：10.1021/ic801352d

  日期：2008.12.1

  reaction of osmium(VIII) oxide with p-substituted aromatic amines (X-C(6)H(4)-NH(2), where X = Me, H, Cl) in heptane afforded the brown osmium(VI)-oxo complexes [OsO(L)(2)] (1a-c, L = N-aryl-1,2-arylenediamide) in moderate yields. The ligand L is formed in situ via oxidative ortho-C-N fusion of arylamines. The reaction occurs in an inert atmosphere, and a part of Os(VIII) is used up for the oxidation of aromatic

  在氧化（（VIII）与对位取代的芳族胺（XC（6）H（4）-NH（2），其中X = Me，H，Cl）在庚烷中的不寻常反应中，得到棕色（VI）-羰基配合物[OsO（L）（2）]（1a-c，L = N-芳基-1,2-芳基二酰胺），产率中等。配体L通过芳基胺的氧化邻-CN融合原位形成。该反应在惰性气氛中进行，Os（VIII）的一部分用尽了以氧化芳香胺。解决了代表性络合物1a的单晶X射线结构。结构分析已验证ArNH（2）的邻-CN融合导致形成了二酰胺配体L。该复合物整体上是五配位的，配位球具有扭曲的方锥几何形状（tau = 0.26） 。氧化（（VIII）与预先形成的N-phenyl-1的相似反应，2-苯甲二胺以接近定量的产率产生复合物1a。作为后一反应的副产物，获得了取代的吩嗪5-苯基-3-苯基亚氨基-3，5-二氢吩嗪-2-基胺。配合物1a-c可以在可逆的单电子步骤中还原，如循环伏安法所示。但是
• 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.
• Barry et al., Journal of the Chemical Society, 1956, p. 893
  作者：Barry et al.

  DOI：——

  日期：——
• Barry; Belton, Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science, 1953, vol. 55B, p. 149,153,155
  作者：Barry、Belton

  DOI：——

  日期：——
• Balogh-Hergovich, E.; Bodnar, G.; Speier, G, Acta Chimica Academiae Scientiarum Hungaricae, 1981, vol. 108, # 1, p. 37 - 42
  作者：Balogh-Hergovich, E.、Bodnar, G.、Speier, G

  DOI：——

  日期：——