7,8-dimethoxyquinoline | 171293-98-4

• 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: 7,8-dimethoxyquinoline
• CAS: 171293-98-4
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: VJZVVNAGXRWKET-UHFFFAOYSA-N

物化性质

• 沸点：
  148-150 °C(Press: 3-4 Torr)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 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：

  7,8-dimethoxyquinoline 在 吡啶 、 溴 作用下， 反应 42.0h， 生成 3,5-dibromo-7,8-dimethoxyquinoline
  参考文献：
  名称：

  Substituted 8-Methoxyquinolines: Regioselective Bromination, Coupling Reactions and Cyclization to an 11H-Indolo[3,2-C]quinoline

  摘要：

  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.

  DOI：

  10.1080/00397919508011477
• 作为产物：
  描述：

  2,3-二甲氧基苯胺 、 甘油 在 硫酸 、 硝基苯 作用下， 生成 7,8-dimethoxyquinoline
  参考文献：
  名称：

  Rajagopalan, Proceedings - Indian Academy of Sciences, Section A, 1941, vol. 13, p. 566,569

  摘要：

  DOI：

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。
• Rajagopalan, Proceedings - Indian Academy of Sciences, Section A, 1941, vol. <A> 13, p. 566,569
  作者：Rajagopalan

  DOI：——

  日期：——
• 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.