3,6-dibromo-4-methyl-2-methoxyquinoline | 1312180-27-0

• 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: 3,6-dibromo-4-methyl-2-methoxyquinoline
• 英文别名: 3,6-Dibromo-2-methoxy-4-methylquinoline；3,6-dibromo-2-methoxy-4-methylquinoline
• CAS: 1312180-27-0
• 化学式: C₁₁H₉Br₂NO
• 分子量: 331.007
• InChiKey: ZQSFPHNATCFTSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 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：

  3,6-dibromo-4-methyl-2-methoxyquinoline 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 3-bromo-2-methoxy-6-(4'-methoxyphenyl)-4-methylquinoline 、 6-bromo-2-methoxy-3-(4'-methoxyphenyl)-4-methylquinoline 、 2-methoxy-3,6-bis(4'-methoxyphenyl)-4-methylquinoline
  参考文献：
  名称：

  Studies of one-pot double couplings on dibromoquinolines

  摘要：

  In a series of studies, the regioselectivity of Suzuki couplings of dibromoquinolines has been investigated. In general, it is much harder to achieve high levels of regioselectivity in these systems compared to many of the other dibromoheteroaromatics that have been studied. Useful levels of selectivity could be achieved for both a 5,7-dibromoquinoline as well as 3,4-dibromoquinoline. Double Suzuki couplings could also be achieved on these two compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.052
• 作为产物：
  描述：

  N-(4-溴苯基)-3-氧丁酰胺 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 ammonium acetate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.67h， 生成 3,6-dibromo-4-methyl-2-methoxyquinoline
  参考文献：
  名称：

  Studies of one-pot double couplings on dibromoquinolines

  摘要：

  In a series of studies, the regioselectivity of Suzuki couplings of dibromoquinolines has been investigated. In general, it is much harder to achieve high levels of regioselectivity in these systems compared to many of the other dibromoheteroaromatics that have been studied. Useful levels of selectivity could be achieved for both a 5,7-dibromoquinoline as well as 3,4-dibromoquinoline. Double Suzuki couplings could also be achieved on these two compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.052

文献信息

• Studies of one-pot double couplings on dibromoquinolines
  作者：Alexander Piala、Diyar Mayi、Scott T. Handy

  DOI：10.1016/j.tet.2011.04.052

  日期：2011.6

  In a series of studies, the regioselectivity of Suzuki couplings of dibromoquinolines has been investigated. In general, it is much harder to achieve high levels of regioselectivity in these systems compared to many of the other dibromoheteroaromatics that have been studied. Useful levels of selectivity could be achieved for both a 5,7-dibromoquinoline as well as 3,4-dibromoquinoline. Double Suzuki couplings could also be achieved on these two compounds. (C) 2011 Elsevier Ltd. All rights reserved.