8-[(2-bromobenzyl)oxy]quinoline | 1155930-10-1

• 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: 8-[(2-bromobenzyl)oxy]quinoline
• 英文别名: 8-(2-bromobenzyloxy)quinoline；8-[(2-Bromophenyl)methoxy]quinoline
• CAS: 1155930-10-1
• 化学式: C₁₆H₁₂BrNO
• mdl: MFCD13201978
• 分子量: 314.181
• InChiKey: NUUOEBMJZTYAIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-[(2-bromobenzyl)oxy]quinoline 在 四丁基溴化铵 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到6H-isochromeno[4,3-h]quinoline
  参考文献：
  名称：

  钯催化的分子内联芳基偶联：苯甲酰化的吡喃喹啉和朱洛力定衍生物的高效途径

  摘要：

  通过钯催化的分子内芳基-芳基交叉偶联反应，已经实现了一种新的合成苯并吡喃喹啉的有效途径。偶联反应在无配体条件下用催化体系Pd（OAc）2 / Cs 2 CO 3 / TBAB进行，收率高。在最佳反应条件下无法获得减少卤素的产物。还描述了5,6-二氢-4 H，8 H-吡啶并[3,2,1- de ]菲啶的区域选择性合成。在后一种情况下，已经观察到碱（Ag 2 CO 3）对转化效率的显着影响。 联芳基偶联-Heck反应-分子内环化-钯催化剂-吡喃喹啉-二氢吡啶并菲啶

  DOI：

  10.1055/s-0028-1083363
• 作为产物：
  描述：

  8-羟基喹啉 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以91%的产率得到8-[(2-bromobenzyl)oxy]quinoline
  参考文献：
  名称：

  Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities

  摘要：

  A series of 8-benzyloxy-substituted quinoline ethers (2a-n) compounds were synthesized. All synthesized compounds were screened in vitro for their preliminary antimicrobial activities against two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), two Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis), and a fungal species (Aspergillus niger). Among all synthesized compounds, compound 2e showed a significant growth inhibitory activity with MIC value 3.125 mu g/mL which was comparable to 8-hydroxyquinoline (2.5 mu g/mL) and terbinafine (1.25 mu g/mL) against A. niger.

  DOI：

  10.1007/s00044-014-1217-4

文献信息

• Palladium-Catalyzed Intramolecular Biaryl Coupling: A Highly Efficient Avenue for Benzannulated Pyranoquinolines and Julolidine Derivatives
  作者：K. Majumdar、Abu Taher、Pradip Debnath

  DOI：10.1055/s-0028-1083363

  日期：——

  efficient route to the synthesis of benzannulated pyranoquinolines has been accomplished via palladium-catalyzed intramolecular aryl-aryl cross-coupling reactions. The coupling reactions proceeded smoothly under ligand-free conditions with the catalytic system Pd(OAc)2/Cs2CO3/TBAB in high yields. Halogen-reduced product was not obtained in optimum reaction conditions. Regioselective synthesis of 5,6-dihydro-4H

  通过钯催化的分子内芳基-芳基交叉偶联反应，已经实现了一种新的合成苯并吡喃喹啉的有效途径。偶联反应在无配体条件下用催化体系Pd（OAc）2 / Cs 2 CO 3 / TBAB进行，收率高。在最佳反应条件下无法获得减少卤素的产物。还描述了5,6-二氢-4 H，8 H-吡啶并[3,2,1- de ]菲啶的区域选择性合成。在后一种情况下，已经观察到碱（Ag 2 CO 3）对转化效率的显着影响。 联芳基偶联-Heck反应-分子内环化-钯催化剂-吡喃喹啉-二氢吡啶并菲啶
• Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities
  作者：Po-Yee Chung、Roberto Gambari、Yi-Xin Chen、Chor-Hing Cheng、Zhao-Xiang Bian、Albert Sun-Chi Chan、Johnny Cheuk-On Tang、Polly Hang-Mei Leung、Chung-Hin Chui、Kim-Hung Lam

  DOI：10.1007/s00044-014-1217-4

  日期：2015.4

  A series of 8-benzyloxy-substituted quinoline ethers (2a-n) compounds were synthesized. All synthesized compounds were screened in vitro for their preliminary antimicrobial activities against two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), two Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis), and a fungal species (Aspergillus niger). Among all synthesized compounds, compound 2e showed a significant growth inhibitory activity with MIC value 3.125 mu g/mL which was comparable to 8-hydroxyquinoline (2.5 mu g/mL) and terbinafine (1.25 mu g/mL) against A. niger.