2-(quinolin-7-yl)aniline | 92437-13-3

• 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-(quinolin-7-yl)aniline
• 英文别名: 2-(Quinolin-7-yl)aniline；2-quinolin-7-ylaniline
• CAS: 92437-13-3
• 化学式: C₁₅H₁₂N₂
• mdl: MFCD25086849
• 分子量: 220.274
• InChiKey: OOEVCXVUIQNEOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(quinolin-7-yl)aniline 在 盐酸 、 sodium nitrite 、 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.5h， 生成 7-(2-azidophenyl)quinoline
  参考文献：
  名称：

  用于抗疟、抗增殖和抗微生物活性的异隐油平和区域异构体的四环系统的合成和评价

  摘要：

  合成了一系列新的基于喹啉的四环系统，并在体外评估了它们的抗疟原虫、抗增殖和抗菌活性。新型氢碘酸盐10和21显示出最有希望的抗疟原虫抑制作用，化合物10显示出比所用标准更高的选择性。抗增殖试验显示新型吡啶并菲啶4b对人前列腺癌 (IC 50 = 24 nM) 的活性明显高于用于临床治疗的嘌呤霉素 (IC 50 = 270 nM) 和多柔比星 (IC 50 = 830 nM)。吡啶并咔唑9对所有采用的癌细胞系也具有中等效果，此外还显示出出色的生物膜抑制（9a：MBIC = 100 µM；9b：MBIC = 100 µM）。

  DOI：

  10.3390/molecules26113268
• 作为产物：
  描述：

  邻氨基苯硼酸盐酸盐 、 7-溴喹啉 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 20.0h， 以82%的产率得到2-(quinolin-7-yl)aniline
  参考文献：
  名称：

  Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers

  摘要：

  Bromoquinolines (2-bromoquinoline - 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C-H activation/C-N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2019.04.026

文献信息

• Remote C−H Olefination of Heterocyclic Biaryls Enabled by Reversibly Bound Templates
  作者：Luo‐Yan Liu、Zhoulong Fan、Md Emdadul Hoque、Shaoqun Qian、Guangrong Meng、Nikita Chekshin、Keita Tanaka、Jennifer X. Qiao、Kap‐Sun Yeung、Jin‐Quan Yu

  DOI：10.1002/anie.202307581

  日期：2023.9.11

  Remote C−H functionalization of heterocyclic biaryls will be of great importance in synthesis and medicinal chemistry. Through adjusting the geometric relationship of the directing atom and target C−H bonds, two new catalytic templates have been developed to enable the functionalization of the more hindered ortho‐C−H bonds of heterobiaryls bearing directing heteroatom at the meta‐ or para‐positions, affording unprecedented site‐selectivity. The use of template chaperone also overcomes product inhibition and renders the directing templates catalytic. The utility of this protocol was demonstrated by olefination of heterocyclic biaryls with various substituents, overriding conventional steric and electronic effects. These ortho‐C−H olefinated heterobiaryls are sterically hindered and can often be challenging to prepare through aryl‐aryl coupling reactions.

  摘要杂环双芳基的远程 C-H 功能化在合成和药物化学中将具有重要意义。通过调整指导原子和目标 C-H 键的几何关系，我们开发出了两种新的催化模板，可以对在元或对位上带有指导杂原子的杂环双芳基中阻碍较大的正 C-H 键进行官能化，从而获得前所未有的位点选择性。模板伴侣的使用还克服了产物抑制作用，并使定向模板具有催化作用。通过对带有各种取代基的杂环双芳基进行烯化反应，证明了这一方案的实用性，克服了传统的立体和电子效应。这些正交-C-H 烯化杂环双芳基具有立体阻碍，通常很难通过芳基-芳基偶联反应制备。
• Mapping the reactivity of the quinoline ring-system – Synthesis of the tetracyclic ring-system of isocryptolepine and regioisomers
  作者：Katja S. Håheim、Ida T. Urdal Helgeland、Emil Lindbäck、Magne O. Sydnes

  DOI：10.1016/j.tet.2019.04.026

  日期：2019.5

  Bromoquinolines (2-bromoquinoline - 8-bromoquinoline and 5-bromo-3-methoxyquinoline) and 2-aminophenylboronic acid hydrochloride were subjected to Suzuki-Miyaura cross-coupling conditions resulting in formation of the desired biaryl systems in good yields. The resulting biaryls were then subjected to palladium catalyzed C-H activation/C-N bond formation utilizing PdCl2(dppf). The reactions revealed large differences in reactivity depending on the attachment point for the 2-aminophenyl group on the quinoline. The variation in the reactivity was rationalized based on the electron distribution around the quinoline ring-system. (C) 2019 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluation of the Tetracyclic Ring-System of Isocryptolepine and Regioisomers for Antimalarial, Antiproliferative and Antimicrobial Activities
  作者：Katja S. Håheim、Emil Lindbäck、Kah Ni Tan、Marte Albrigtsen、Ida T. Urdal Helgeland、Clémence Lauga、Théodora Matringe、Emily K. Kennedy、Jeanette H. Andersen、Vicky M. Avery、Magne O. Sydnes

  DOI：10.3390/molecules26113268

  日期：——

  A series of novel quinoline-based tetracyclic ring-systems were synthesized and evaluated in vitro for their antiplasmodial, antiproliferative and antimicrobial activities. The novel hydroiodide salts 10 and 21 showed the most promising antiplasmodial inhibition, with compound 10 displaying higher selectivity than the employed standards. The antiproliferative assay revealed novel pyridophenanthridine

  合成了一系列新的基于喹啉的四环系统，并在体外评估了它们的抗疟原虫、抗增殖和抗菌活性。新型氢碘酸盐10和21显示出最有希望的抗疟原虫抑制作用，化合物10显示出比所用标准更高的选择性。抗增殖试验显示新型吡啶并菲啶4b对人前列腺癌 (IC 50 = 24 nM) 的活性明显高于用于临床治疗的嘌呤霉素 (IC 50 = 270 nM) 和多柔比星 (IC 50 = 830 nM)。吡啶并咔唑9对所有采用的癌细胞系也具有中等效果，此外还显示出出色的生物膜抑制（9a：MBIC = 100 µM；9b：MBIC = 100 µM）。