3-bromo-6-methoxy-8-methylquinoline

• 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: 3-bromo-6-methoxy-8-methylquinoline
• 英文别名: 3-Bromo-6-methoxy-8-methylquinoline
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: WWHIJUGIODDUEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-bromo-6-methoxy-8-methylquinoline 在 氢溴酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-(3-bromo-8-methylquinolin-6-yloxy)-2-methylsulfanylacetic acid methyl ester
  参考文献：
  名称：

  Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors

  摘要：

  A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.

  DOI：

  10.1016/j.bmc.2014.06.015
• 作为产物：
  描述：

  2,2,3-三溴丙醛 、 2-甲基-4-甲氧基苯胺 在 溶剂黄146 作用下， 反应 6.0h， 以45%的产率得到3-bromo-6-methoxy-8-methylquinoline
  参考文献：
  名称：

  Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors

  摘要：

  A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.

  DOI：

  10.1016/j.bmc.2014.06.015

文献信息

• 2,2,3-Tribromopropanal as a Versatile Reagent in the Skraup-Type Synthesis of 3-Bromoquinolin-6-ols
  作者：Clemens Lamberth、Fiona Kessabi、Renaud Beaudegnies、Laura Quaranta、Stephan Trah、Guillaume Berthon、Fredrik Cederbaum、Thomas Vettiger、CS Prasanna

  DOI：10.1055/s-0033-1340670

  日期：——

  2,2,3-Tribromopropanal, a reagent which almost became forgotten in the chemical literature after its first application in the 1950s, is used for the one-step transformation of diversely substituted 4-nitro- and 4-methoxyanilines into 3-bromo-6-nitroquinolines and 3-bromo-6-methoxyquinolines. These intermediates are then converted, in one further step, into 3-bromoquinolin-6-ols, which may carry additional substituents at positions 7 and 8.
• Synthesis and fungicidal activity of quinolin-6-yloxyacetamides, a novel class of tubulin polymerization inhibitors
  作者：Clemens Lamberth、Fiona Murphy Kessabi、Renaud Beaudegnies、Laura Quaranta、Stephan Trah、Guillaume Berthon、Fredrik Cederbaum、Gertrud Knauf-Beiter、Valeria Grasso、Stephane Bieri、Andy Corran、Urvashi Thacker

  DOI：10.1016/j.bmc.2014.06.015

  日期：2014.8

  A novel class of experimental fungicides has been discovered, which consists of special quinolin-6-yloxyacetamides. They are highly active against important phytopathogens, such as Phytophthora infestans (potato and tomato late blight), Mycosphaerella graminicola (wheat leaf blotch) and Uncinula necator (grape powdery mildew). Their fungicidal activity is due to their ability to inhibit fungal tubulin polymerization, leading to microtubule destabilization. An efficient synthesis route has been worked out, which allows the diverse substitution of four identified key positions across the molecular scaffold.