5-chloro-3-methyl-2-nitroaniline | 131885-36-4

• 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: 5-chloro-3-methyl-2-nitroaniline
• CAS: 131885-36-4
• 化学式: C₇H₇ClN₂O₂
• 分子量: 186.598
• InChiKey: UZZYMOHCRGMSCN-UHFFFAOYSA-N

物化性质

• 沸点：
  329.5±37.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-methyl-2-nitroaniline 在 镍 氢气 作用下， 以 甲醇 为溶剂， 25.0~180.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 5-(2,4-Dimethylimidazol-1-yl)-3-methylbenzene-1,2-diamine
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024
• 作为产物：
  描述：

  3,5-二氯-2-硝基甲苯 在 氨 作用下， 以 乙二醇甲醚 为溶剂， 150.0 ℃ 、3.3 MPa 条件下， 反应 72.0h， 以63%的产率得到5-chloro-3-methyl-2-nitroaniline
  参考文献：
  名称：

  Cardiotonic agents. Synthesis and cardiovascular properties of novel 2-arylbenzimidazoles and azabenzimidazoles

  摘要：

  Novel 2-arylbenzimidazoles and azabenzimidazoles were synthesized, and their inotropic action was evaluated. Changes in left ventricular pressure, dP/dt max, were measured as an index of cardiac contractility. The structural features that impart optimal inotropic activity are presented. The most potent compounds were evaluated orally in conscious dogs with implanted Konigsberg pressure transducers. To investigate the mechanism of action, the most potent compounds were tested for their calcium-sensitizing properties and their potential for the inhibition of phosphodiesterase. Two compounds, 1 and 4 1, showed interesting in vitro and oral activity without side effects. They have a more potent calcium-sensitizing effect than MCI-154 and are under futher investigation.

  DOI：

  10.1021/jm00101a024

文献信息

• Quaternization of azido-N-heteroarenes with Meerwein reagent: A straightforward synthesis of 2-azido(benzo)imidazolium and related azido-N-heteroarenium tetrafluoroborates
  作者：Yan Li、Ting-Biao Wan、Bin Guo、Xiao-Wen Qi、Chifan Zhu、Mei-Hua Shen、Hua-Dong Xu

  DOI：10.1016/j.tetlet.2022.154063

  日期：2022.9

  2-Azido(benzo)imidazolium salts have been made through quaternization of 2-Azido(benzo)imidazoles with Meerwein reagent at ambient conditions. This one-pot protocol is also applicable to 4 or 3-azidopyridines and appropriate azido(iso)quinolines to prepare correlative azido-N-heteroarenium salts. When compared with their precursors, improved diazotransfer reactivity was observed for several representative

  2-叠氮基（苯并）咪唑鎓盐是通过在环境条件下用 Meerwein 试剂对 2-叠氮基（苯并）咪唑进行季铵化制备的。这种一锅法也适用于 4 或 3-叠氮基吡啶和适当的叠氮基（异）喹啉，以制备相关的叠氮基-N-杂芳基盐。与它们的前体相比，观察到几种代表性叠氮基-N-杂芳烃盐与丙二酸二乙酯反应的重氮转移反应性有所提高。