5-bromo-7,8-dimethoxyquinoline | 170959-57-6

• 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-7,8-dimethoxyquinoline
• 英文别名: Quinoline, 5-bromo-7,8-dimethoxy-
• CAS: 170959-57-6
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: MHBMOGUOXIDSRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-7,8-dimethoxyquinoline 在 四(三苯基膦)钯 、 硫酸 、 potassium carbonate 作用下， 反应 6.5h， 生成 5-(2-amino-5-methoxyphenyl)-7,8-dimethoxyquinoline
  参考文献：
  名称：

  由5-溴-8-甲氧基喹啉经偶联和叠氮环化反应合成7 H-吡啶并[2,3- c ]咔唑

  摘要：

  通过与（2-氨基苯基）硼酸的交叉偶联反应，然后进行区域选择性叠氮化物环化，由取代的5-溴喹啉开发了一种合成取代的7 H-吡啶并[2,3- c ]咔唑的新策略。

  DOI：

  10.1002/jhet.5570320428
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 sodium hydroxide 、 四丁基碘化铵 、 potassium carbonate 、 苯基锂 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 生成 5-bromo-7,8-dimethoxyquinoline
  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。
• Significant Enhancement of the Stille Reaction with a New Combination of Reagents—Copper(I) Iodide with Cesium Fluoride
  作者：Simon P. H. Mee、Victor Lee、Jack E. Baldwin

  DOI：10.1002/chem.200401162

  日期：2005.5.20

  The combination of copper(I) iodide and cesium fluoride significantly enhances the Stille reaction. After extensive optimisation, a variety of electronically unfavourable and sterically hindered substrates were coupled in very high yields under mild conditions.

  碘化铜（I）和氟化铯的组合显着增强了斯蒂勒反应。经过广泛的优化后，在温和的条件下，以很高的收率耦合了各种电子上不利且空间受阻的底物。
• Rapid and convergent assembly of the polycyclic framework assigned to the cytotoxic marine alkaloid halitulin
  作者：Martin G. Banwell、Andrew M. Bray、Alison J. Edwards、David J. Wong

  DOI：10.1039/b111401h

  日期：2002.5.23

  Compound 3, representing the tetra-O-methyl ether derivative of structure, 1, assigned to the cytotoxic marine alkaloid halitulin, has been assembled in a convergent manner from the readily available building blocks 5, 6 and 11.

  化合物 3 是结构 1 的四-O-甲基醚衍生物，属于具有细胞毒性的海洋生物碱 halitulin，由现成的结构单元 5、6 和 11 以聚合的方式组装而成。
• Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion
  作者：Simon P. H. Mee、Victor Lee、Jack E. Baldwin

  DOI：10.1002/anie.200352979

  日期：2004.2.20
• Substituted 8-Methoxyquinolines: Regioselective Bromination, Coupling Reactions and Cyclization to an 11<i>H</i>-Indolo[3,2-C]quinoline
  作者：Francois Trécourt、Florence Mongin、Marc Mallet、Guy Quéguiner

  DOI：10.1080/00397919508011477

  日期：1995.12

  5,7-Disubstituted 8-methoxyquinolines were brominated at C-3 position. The palladium-catalyzed cross-coupling of obtained 3-bromoquinolines with phenylboric acids gave corresponding 3-arylquinolines from which a substituted 11H-indolo[3,2-c]quinoline could be synthesized.