2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole | 36939-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
• 英文别名: 2-p-tolyl-1H-phenanthro[9,10-d] imidazole；2-p-tolyl-1H-phenanthro[9,10-d]imidazole；2-p-tolyl-1H-phenanthro[9,10-d]imidazole；2-p-Tolyl-phenanthro<9.10-d>imidazol；2-(4-methylphenyl)-1H-phenanthro[9,10-d]imidazole
• CAS: 36939-53-4
• 化学式: C₂₂H₁₆N₂
• 分子量: 308.382
• InChiKey: PMBSLRLCVWAKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole 生成 2-methoxy-2-p-tolyl-2H-phenanthro[9,10-d]imidazole
  参考文献：
  名称：

  KAKISAWA H.; KUSUMI T., J. HETEROCYCL. CHEM. , 1975, 12, NO 5, 953-956

  摘要：

  DOI：
• 作为产物：
  描述：

  3-p-tolylphenanthro[9,10-e][1,2,4]triazine 在 环己烯 作用下， 500.0 ℃ 、6.0 Pa 条件下， 反应 0.25h， 以38%的产率得到2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
  参考文献：
  名称：

  缩合的1,2,4-三嗪的气相热解：通往杂环系统的有趣途径

  摘要：

  噻吩并[2,3- e ] [1,2,4]三嗪在气相中热解得到苄腈，异噻唑，哒嗪和噻吩并[2,3- d ]噻唑衍生物。苯并[1,2,4]三嗪和菲[9,10- e ] [1,2,4]三嗪衍生物通过与硫一起在350°C加热而相似地转化为相应的缩合噻唑。提出了这些热解转化的机理。

  DOI：

  10.1016/j.tet.2007.10.040

文献信息

• Study on the synthesis and structure-effect relationship of multi-aryl imidazoles with their fluorescence properties
  作者：Mi Tian、Chao Wang、LiGong Wang、Kai Luo、An Zhao、CanCheng Guo

  DOI：10.1002/bio.2580

  日期：2014.8

  In this paper, 23 multi-aryl imidazole derivatives were synthesized and identified by nuclear magnetic resonance, ultraviolet-visible and elemental analysis. At the same time, their ultraviolet-visible maximum absorption (λabmax), fluorescence emission maximum (λemmax) and quantum yields (Фf) were measured. The relationships between the optical behaviors and structures for these compounds were assessed. The results show that the λmaxab and λmaxem are red-shifted and the fluorescence Фf are increased by the introduction of electron-withdrawing substituents and the increase in the planarity of multi-aryl imidazole molecules. The results also showed that the fluorescence quantum yields of the compounds containing two imidazole nuclei are double the corresponding mono-imidazole nucleus compounds. Copyright © 2013 John Wiley & Sons, Ltd.

  在本论文中，合成了23种多芳基咪唑衍生物并通过核磁共振、紫外-可见光谱和元素分析进行了鉴定。同时，测量了它们的紫外-可见最大吸收（λabmax）、荧光发射最大值（λemmax）和量子产率（Фf）。评估了这些化合物的光学行为与结构之间的关系。结果表明，通过引入吸电子取代基和增加多芳基咪唑分子的平面性，λmaxab和λmaxem发生红移，荧光Фf增加。结果还显示，含有两个咪唑核的化合物的荧光量子产率是对应的单咪唑核化合物的两倍。版权所有 © 2013 John Wiley & Sons, Ltd。
• FRET-Based Probe for Monitoring pH Changes in Lipid-Dense Region of Hct116 Cells
  作者：Upendar Reddy G、Anila H. A、Firoj Ali、Nandaraj Taye、Samit Chattopadhyay、Amitava Das

  DOI：10.1021/acs.orglett.5b02568

  日期：2015.11.20

  A rhodamine conjugate (L) with a pseudo Stokes shift of 165 nm is used for probing changes in solution pH under physiological conditions. This reagent is found to be nontoxic, and the luminescence response could be used for imaging changes in endogenous pH induced by dexamethanose (DMT) in the endoplasmic reticulum.

  具有伪斯托克斯位移为165 nm的罗丹明缀合物（L）用于探测生理条件下溶液pH的变化。发现该试剂是无毒的，并且发光反应可用于成像内质网中地塞米糖（DMT）诱导的内源性pH的变化。
• Construction of Fluorescent Probes Via Protection/Deprotection of Functional Groups: A Ratiometric Fluorescent Probe for Cu²⁺
  作者：Weiying Lin、Lin Yuan、Wen Tan、Jianbo Feng、Lingliang Long

  DOI：10.1002/chem.200801501

  日期：2009.1.12

  Herein a ratiometric fluorescent Cu2+ probe was rationally constructed in a straightforward manner with the concept of aldehyde group protection/deprotection. The probe showed a ratiometric fluorescent response to Cu2+ with a large emission wavelength shift (>100 nm) and displayed high selectivity for Cu2+ over other metal ions due to distinct deprotection conditions. In addition, a Cu2+‐promoted dethioacetalization

  在此，以醛基保护/脱保护的概念以直接的方式合理地构造了比率式荧光Cu 2+探针。该探针显示出对Cu 2+的比例荧光响应，具有较大的发射波长偏移（> 100 nm），并且由于独特的脱保护条件，对Cu 2+的选择性高于其他金属离子。另外，提出了一种Cu 2+促进的脱硫缩醛化机理。
• A Ratiometric Fluorescent Probe for Hypochlorite Based on a Deoximation Reaction
  作者：Weiying Lin、Lingliang Long、Bingbing Chen、Wen Tan

  DOI：10.1002/chem.200802054

  日期：2009.2.23

  The first ratiometric fluorescent probe for hypochlorite has been developed through regulation of the electron‐withdrawing ability of the electron acceptor in an intramolecular charge‐transfer (ICT) system by a deoximation reaction (see figure; EWG=electron‐withdrawing group).

  通过脱氧反应调节分子内电荷转移（ICT）系统中电子受体的吸电子能力，开发出了第一款用于次氯酸盐的比例荧光探针。
• New approach to the multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazoles
  作者：Saman Damavandi

  DOI：10.1515/hc.2011.018

  日期：2011.1.1

  Abstract A novel, acid catalyzed multicomponent one-pot synthesis of 2-aryl-1H-phenanthro[9,10-d]imidazole compounds derived from aromatic aldehydes, 9,10-phenanthrenequinone and ammonium acetate under ultrasonic irradiation is reported. A wide range of aromatic aldehydes readily undergo condensation with 9,10-phenanthrenequinone and ammonium acetate under optimized conditions to afford the desired

  摘要报道了一种新型的酸催化多组分一锅法合成由芳香醛、9,10-菲醌和醋酸铵衍生的 2-芳基-1H-菲[9,10-d]咪唑化合物在超声辐照下。在优化的条件下，多种芳香醛很容易与 9,10-菲醌和乙酸铵缩合，从而以优异的收率提供所需的高纯度咪唑。