1,1'-(5-nitro-1,3-phenylene)bis(1H-imidazole) | 1013655-23-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,1'-(5-nitro-1,3-phenylene)bis(1H-imidazole)
• CAS: 1013655-23-6
• 化学式: C₁₂H₉N₅O₂
• 分子量: 255.236
• InChiKey: DACZFVBZALZJLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.78
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1'-(5-nitro-1,3-phenylene)bis(1H-imidazole) 在 吡啶 、 tin(II) chloride dihdyrate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (R)-2-(3,5-di(1H-imidazol-1-yl)amino)-2-oxo-1-phenylethyl acetate
  参考文献：
  名称：

  A bifunctional metal–organic framework platform for catalytic applications

  摘要：

  DUT-71 (DUT- Dresden University of Technology), a copper paddle wheel based framework, was used as a platform for postsynthetic modification to introduce specific catalytically active sites and to enhance the catalytic activity for fine chemicals production using bifunctional N-donor ligands such as dabco (1,4-diazabicyclo[2.2.2]octane) and 3,5-bis(1H-imidazol-1-yl)arene derivatives resulting in the corresponding networks DUT-72 and DUT-90. The intact network structure after functionalisation was confirmed by powder X-ray diffraction, the degree of functionalization was analysed by H-1 NMR, thermal and elemental analysis. As a model reaction, the C-C coupling reaction of Henry type catalysed by Lewis acids in presence of organic base was chosen. The influence of the functionalisation degree, solvent, and reaction temperature on the catalytic activities was studied. Finally, yields up to 77% of 2-nitro-1-(4nitrophenyl)ethan-1-ol in the reaction of 4-nitrobenzaldeyde with nitromethane were achieved using a dabco functionalised network DUT-72. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.11.003
• 作为产物：
  描述：

  2,6-二溴-4-硝基苯胺 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 硫酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 132.0h， 生成 1,1'-(5-nitro-1,3-phenylene)bis(1H-imidazole)
  参考文献：
  名称：

  A bifunctional metal–organic framework platform for catalytic applications

  摘要：

  DUT-71 (DUT- Dresden University of Technology), a copper paddle wheel based framework, was used as a platform for postsynthetic modification to introduce specific catalytically active sites and to enhance the catalytic activity for fine chemicals production using bifunctional N-donor ligands such as dabco (1,4-diazabicyclo[2.2.2]octane) and 3,5-bis(1H-imidazol-1-yl)arene derivatives resulting in the corresponding networks DUT-72 and DUT-90. The intact network structure after functionalisation was confirmed by powder X-ray diffraction, the degree of functionalization was analysed by H-1 NMR, thermal and elemental analysis. As a model reaction, the C-C coupling reaction of Henry type catalysed by Lewis acids in presence of organic base was chosen. The influence of the functionalisation degree, solvent, and reaction temperature on the catalytic activities was studied. Finally, yields up to 77% of 2-nitro-1-(4nitrophenyl)ethan-1-ol in the reaction of 4-nitrobenzaldeyde with nitromethane were achieved using a dabco functionalised network DUT-72. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2018.11.003

文献信息

• From rigid cyclic templates to conformationally stabilized acyclic scaffolds. Part I: The discovery of CCR3 antagonist development candidate BMS-639623 with picomolar inhibition potency against eosinophil chemotaxis
  作者：Joseph B. Santella、Daniel S. Gardner、Wenqing Yao、Chongsheng Shi、Prabhakar Reddy、Andrew J. Tebben、George V. DeLucca、Dean A. Wacker、Paul S. Watson、Patricia K. Welch、Eric A. Wadman、Paul Davies、Kimberly A. Solomon、Dani M. Graden、Swamy Yeleswaram、Sandhya Mandlekar、Ilona Kariv、Carl P. Decicco、Soo S. Ko、Percy H. Carter、John V. Duncia

  DOI：10.1016/j.bmcl.2007.11.067

  日期：2008.1

  Conformational analysis of trans-1,2-disubstituted cyclohexane CCR3 antagonist 2 revealed that the cyclohexane linker could be replaced by an acyclic syn-alpha-methyl-beta-hydroxypropyl linker. Synthesis and biological evaluation of mono- and disubstituted propyl linkers support this conformational correlation. It was also found that the alpha-methyl group to the urea lowered protein binding and that

  反式1,2-二取代的环己烷CCR3拮抗剂2的构象分析表明，环己烷接头可被无环的顺式α-甲基-β-羟丙基接头取代。单取代和双取代丙基连接基的合成和生物学评估支持这种构象相关性。还发现与尿素的α-甲基降低了蛋白结合，而β-羟基降低了对CYP2D6的亲和力。从头算计算表明，α-甲基基团控制着分子内三个关键功能的空间取向。具有嗜酸性粒细胞趋化性IC（50）= 38 pM的α-甲基-β-羟丙基尿素31被选择进入临床治疗哮喘的研究。
• 一种基于芳香环刚性间隔基对称双阳离子咪唑类离子液体及其制备方法
  申请人：湖南大学

  公开号：CN116283784A

  公开（公告）日：2023-06-23

  本发明公开了一种含芳香环刚性间隔基的对称双阳离子咪唑类离子液体及其制备方法，所述双阳离子离子液体具有双咪唑环结构作为阳离子基团、芳香环作为间隔基、两端为两条烷基链，具有一个二价的阳离子和两个游离的阴离子。离子液体的阳离子结构通式如下： 阴离子Z化学性能稳定性、极性可调、阴离子交换便捷等特点。