3-溴-8-甲基喹啉-6-醇 | 889660-65-5

• 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
• 中文名称: 3-溴-8-甲基喹啉-6-醇
• 英文名称: 3-bromo-8-methylquinolin-6-ol
• 英文别名: 3-bromo-6-hydroxy-8-methylquinoline；3-bromo-8-methyl-6-hydroxyquinoline；3-bromo-8-methyl-quinolin-6-ol
• CAS: 889660-65-5
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: FUUJWAFBLPHKIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  3-溴-8-甲基喹啉-6-醇 在 lithium hydroxide monohydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(3-bromo-8-methylquinolin-6-yloxy)butyric acid
  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：

  4-硝基-2-甲苯胺 在 盐酸 、 磷酸 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 75.0h， 生成 3-溴-8-甲基喹啉-6-醇
  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

• [EN] QUINOLINE DERIVATIVES AS FUNGICIDES<br/>[FR] DÉRIVÉS DE QUINOLÉINE UTILISÉS EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011154240A1

  公开（公告）日：2011-12-15

  Compounds of the general formula (I) wherein the substituents are as defined in claim 1, are useful as fungicides.

  通式（I）中取代基如权利要求1所定义的化合物，可用作杀真菌剂。
• Synthesis of conformationally locked analogs of quinolin-6-yloxyacetamide fungicides
  作者：Fiona Murphy Kessabi、Renaud Beaudegnies、Laura Quaranta、Clemens Lamberth

  DOI：10.1016/j.tetlet.2016.10.104

  日期：2016.12

  Three different synthesis pathways delivered novel tricyclic compounds which are conformationally locked analogs of quinolin-6-yloxyacetamide fungicides by cyclization of their acetal or O,S-acetal function to quinoline positions 5 or 7. Examples of the fused ring systems of [1,3]oxathiano[6,5-g]quinoline and [1,3]oxathiocino[6,7-f]quinoline, which have been unknown to the chemical literature before

  三种不同的合成途径提供了新颖的三环化合物，它们是通过将其缩醛或O，S-乙缩醛功能环化为喹啉5或7位而成为喹啉-6-酰氧基乙酰胺类杀菌剂的构象锁定类似物。本文首次报道了以前化学文献中还不知道的] oxathiano [6,5- g ]喹啉和[1,3 ]氧代硫辛基[6,7- f ]喹啉。
• Quinoline derivatives as fungicides
  申请人：Syngenta Participations AG

  公开号：EP2397467A1

  公开（公告）日：2011-12-21

  Compounds of the general formula wherein the substituents are as defined in claim 1, are useful as fungicides.

  通式为的化合物，其中取代基如权利要求书中定义的那样，可用作杀真菌剂。
• Synthesis of Linker Isomers of Quinolin-6-yloxyacetamide Fungicides through Newman–Kwart Rearrangement
  作者：Clemens Lamberth、Fiona Kessabi、Laura Quaranta、Renaud Beaudegnies

  DOI：10.1055/s-0035-1561564

  日期：——

  Novel quinolin-6-ylthioacetamides and quinolin-6-ylpropanamides have been prepared. They are linker isomers of quinolin-6-yloxyacetamide fungicides in which the oxygen atom of the O,S-acetal in the original lead structures has been replaced by either a sulfur atom or a methylene bridge. The Newman–Kwart rearrangement proved to be highly useful for the concise synthesis of the quinolin-6-ylthioacetamides

  已经制备了新型喹啉-6-基硫代乙酰胺和喹啉-6-基丙酰胺。它们是 quinolin-6-yloxyacetamide 杀真菌剂的连接异构体，其中原始先导结构中 O,S-缩醛的氧原子已被硫原子或亚甲基桥取代。Newman-Kwart 重排被证明对于从可用的喹啉醇结构单元简明合成喹啉-6-基硫代乙酰胺非常有用。
• Acetamide Compounds as Fungicides
  申请人：Salmon Roger

  公开号：US20080171767A1

  公开（公告）日：2008-07-17

  Compounds of the general formula (I); wherein the substituents are as defined in claim 1 , are useful as fungicides.

  通式为（I）的化合物，其中取代基如权利要求1所定义，可用作杀真菌剂。