5-bromo-7-hydroxy-8-methoxyquinoline | 171293-95-1

• 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: 5-bromo-7-hydroxy-8-methoxyquinoline
• 英文别名: 5-Bromo-8-methoxyquinolin-7-ol
• CAS: 171293-95-1
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: OXNXJPULAHUVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-7-hydroxy-8-methoxyquinoline 在 萘 、 lithium 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 [3,4-Bis(7,8-dimethoxyquinolin-5-yl)pyrrol-1-yl]-tri(propan-2-yl)silane
  参考文献：
  名称：

  Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

  摘要：

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00637-3
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 sodium hydroxide 、 四丁基碘化铵 、 苯基锂 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 5-bromo-7-hydroxy-8-methoxyquinoline
  参考文献：
  名称：

  Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

  摘要：

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00637-3

文献信息

• Synthesis of Substituted 8-Methoxyquinolines by Regioselective Bromine-Lithium Exchange of 5,7-Dihalo-8-methoxyquinolines and 7-Bromo-8-methoxyquinoline
  作者：François Trécourt、Marc Mallet、Florence Mongin、Guy Quéguiner

  DOI：10.1055/s-1995-4053

  日期：1995.9

  Reaction of phenyllithium with 7-bromo-8-methoxyquinoline, 5,7-dibromo-8-methoxyquinoline and 5,7-diiodo-8-metehoxyquinoline has been studied. Thus, bromine-lithium exchange of 7-bromo-8-methoxyquinoline gave the 7-lithio-8-methoxyquinoline which reacted with various electrophiles to afford 7-substituted-8-methoxyquinolines 3a-e. The same procedure was also applied to 5,7-dibromo-8-methoxyquinoline, which because of the high regioselectivity of the reaction, led to 7-substituted 5-bromo-8-methoxyquinolines 4a-f; one of them was used for the preparation of a pyridopyranoquinoline.

  苯基锂与7-溴-8-甲氧基喹啉、5,7-二溴-8-甲氧基喹啉及5,7-二碘-8-甲氧基喹啉的反应已被研究。因此，7-溴-8-甲氧基喹啉的溴锂交换生成7-锂代-8-甲氧基喹啉，其与多种亲电试剂反应得到7-取代-8-甲氧基喹啉3a-e。同样的步骤也应用于5,7-二溴-8-甲氧基喹啉，由于反应的高度位选择性，得到了7-取代的5-溴-8-甲氧基喹啉4a-f；其中一种用于制备吡啶并吡喃喹啉。