2,5-bis((4-isopropyl-phenyl)amino)-[1,4]benzoquinone | 351066-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-bis((4-isopropyl-phenyl)amino)-[1,4]benzoquinone
• 英文别名: 2,5-di-[4'-(isopropyl)-anilino]-1,4-benzoquinone；2,5-bis[4-(isopropyl)anilino]-1,4-benzoquinone；2,5-Bis(4-propan-2-ylanilino)cyclohexa-2,5-diene-1,4-dione
• CAS: 351066-64-3
• 化学式: C₂₄H₂₆N₂O₂
• 分子量: 374.483
• InChiKey: NUJZIBSGEKUFGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二溴吡啶 、 十羰基二铼 、 2,5-bis((4-isopropyl-phenyl)amino)-[1,4]benzoquinone 以 甲苯 、 均三甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Utilizing a series of fac-Re(CO)3 core based quinonoid containing complexes for photophysical and cell imaging studies

  摘要：

  A series of N boolean AND O bis-chelating bridging quinone ligands (H2L1, H2L2 and H2L3) have been utilized to synthesize four dinuclear fac-Re(CO)(3) based neutral complexes (1-4) by their reaction with Re(CO)(5)(OTf), where the N-donors 4-dimethylaminopyridine (for 1), 3,5-dibromopyridine (for 2) and acetonitrile (for 3 and 4) act as ancillary ligands. The complexes were characterized by FTIR, H-1 NMR, ESI-MS and elemental analysis. The structures of complexes 1-3 were analysed by X-ray diffraction methods. Photophysical investigations revealed that all the complexes display strong visible-light absorption with absorption maxima at around 500 nm (epsilon = 40000-50000 M-1 cm(-1)), whereas in the solid state the complexes display high intensity broad bands in the entire UV-Vis-NIR region. Complexes 1-4 were found to be luminescent in fluid solutions at room temperature. Favorable photophysical properties allowed their utilization as luminescent probes for live-cell imaging using HeLa cells, where complexes 2 and 4 were found to display good cellular uptake with co-localization in lysosomal compartments, which was observed as yellow fluorescence. Complexes 2 and 4 displayed very low cytotoxicity, as suggested by LDH production experiments. The photophysical properties, uptake pathway, localization properties and cytotoxicity of the complexes are discussed in detail. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.06.030
• 作为产物：
  描述：

  4-异丙基苯胺 、 2,5-二羟基-1,4-苯喹酮 在 溶剂黄146 作用下， 反应 4.0h， 以14%的产率得到2,5-bis((4-isopropyl-phenyl)amino)-[1,4]benzoquinone
  参考文献：
  名称：

  喹诺酮桥联的Diiron（II）配合物中的双稳态：桥对称性对双稳态的影响

  摘要：

  醌型桥非常适合生成可能显示各种双稳态特性的双核组件。在这一贡献中，我们提出了两个二铁（II）配合物，其中铁（II）中心被对称取代的醌型桥2,5-双[4-（异丙基）苯胺基] -1,4的双去质子化形式桥接-具有[O，N，O，N]供体的苯醌（H 2 L2'），或具有不对称取代的醌类桥的双去质子化形式2- [4-（异丙基苯胺基）-5-羟基- 1,4-苯醌（H 2 L5'）的[O，O，O，N]施主集。两种配合物均显示出温度诱导的自旋交叉（SCO）。SCO的性质在很大程度上取决于桥接配体，只有具有[O，O，O，N]供体的配合物显示出约55 K的显着滞后环。重要的是，只有后者的配合物也显示出明显的滞后性。光诱导的自旋状态改变。此外，两种络合物均可被氧化成混合价的铁（II）-铁（III）形式，桥的性质决定了这些形式的Robin和Day分类。两种配合物均已通过一系列电化学，光谱和磁性方法探查，并且该组合方法用于阐明配合物的电子结构和双稳性。

  DOI：

  10.1021/acs.inorgchem.6b02097

文献信息

• Multiple phenyl ring appended Re-based complexes for strong visible light absorption and DNA binding
  作者：Bholey Singh、Balaram Pani、Deepak Gupta

  DOI：10.1039/d1dt02216d

  日期：——

  phenyl rings. All the complexes displayed strong absorption (ε = 14 000–40 000 M−1 cm−1) over wide visible region (400–600 nm). Due to the interesting structural and photophysical properties of the complexes, a satisfactory DNA binding ability was observed. The binding of the complexes with DNA grooves was confirmed by a significant increase in the absorption intensities of the complexes in the visible region

  合成并表征了一系列具有 N∩O 双螯合配体和三苯基膦氧化物供体的面状-Re(CO) 3基无环配合物 ( 1–3 )。这些配合物最有趣的结构特征是两个配位配体均通过外部苯环进行功能化。单晶 X 射线衍射分析证实，每个分子都通过外部苯环表现出多种分子间超分子相互作用。所有配合物在宽可见光区域（400–600 nm）均表现出强吸收（ ε = 14 000–40 000 M -1 cm -1 ）。由于复合物有趣的结构和光物理特性，观察到了令人满意的 DNA 结合能力。通过复合物在可见光区域的吸收强度的显着增加、DNA的吸收增强和圆二色性证实了复合物与DNA凹槽的结合。
• Diamination by N-coupling using a commercial laccase
  作者：Kevin W. Wellington、Paul Steenkamp、Dean Brady

  DOI：10.1016/j.bmc.2010.01.025

  日期：2010.2

  Nuclear diamination of p-hydrobenzoquinones with aromatic and aliphatic primary amines was catalysed by an immobilised commercial laccase, Denilite (R) II Base, from Novozymes. The amine and the p-hydrobenzoquinone was reacted under mild conditions (at room temperature and at 35 degrees C) in a reaction vessel open to air in the presence of laccase and a co-solvent to afford, exclusively, the diaminated p-benzoquinone. These compounds may have potential antiallergic, antibiotic, anticancer, antifungal, antiviral and/or 5-lipoxygenase inhibiting activity. (C) 2010 Elsevier Ltd. All rights reserved.