2-nitro-11-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline | 1563083-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-nitro-11-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline
• CAS: 1563083-76-0
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: LIXPGQKGCDZBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-硝基二苯甲酮 、 环庚酮 在 sulfated polyborate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以84%的产率得到2-nitro-11-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline
  参考文献：
  名称：

  硫酸化聚硼酸酯催化选择性 Friedlander 环化合成高度官能化的喹啉

  摘要：

  由于其广泛的生物活性，喹啉部分是一种特殊的支架。1 , 2 与 Friedlander 环化法一起，开发了用于合成……的其他程序。

  DOI：

  10.1080/00304948.2020.1762457

文献信息

• Design, synthesis and evaluation of acridine and fused-quinoline derivatives as potential anti-tuberculosis agents
  作者：Gisela C. Muscia、Graciela Y. Buldain、Silvia E. Asís

  DOI：10.1016/j.ejmech.2013.12.013

  日期：2014.2

  The synthesis of twelve acridine and polycyclic acridine derivatives prepared via the Friedlander reaction is described. The one-pot reactions of 2-amino-5-chloro or 5-nitro-benzophenones and a variety of cydanones and indanones were carried out in a MW oven under TFA catalysis in good yields. The products were designed according natural antituberculosis products and were evaluated for growth inhibitory activity towards Mycobacterium tuberculosis H(37)Rv (Mtb) through the National Institute of Allergy and Infectious Diseases (NIAID, USA). Three of them underwent additional testings. The cyclopenta[b]quinoline derivative 9 and the acridine derivative 13 showed remarkable MIC values against the rifampin resistant strain. The former exhibited bactericidal activity at 50 mu g/mL, its intracellular activity is similar to rifampin and it was not cytotoxic at low concentrations so it can be considered a new lead compound. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Sulfated Polyborate Catalyzed Selective Friedlander Annulation for Synthesis of Highly Functionalized Quinolines
  作者：Anil S. Mali、Abhishek B. Sharma、Ganesh U. Chaturbhuj

  DOI：10.1080/00304948.2020.1762457

  日期：2020.7.3

  The quinoline moiety is a privileged scaffold because of the wide spectrum of its biological activities. 1 , 2 Along with the Friedlander annulation, other procedures developed for the synthesis of...

  由于其广泛的生物活性，喹啉部分是一种特殊的支架。1 , 2 与 Friedlander 环化法一起，开发了用于合成……的其他程序。