1-amino-3-(2-bromoethoxy)quinoline | 143102-11-8

• 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: 1-amino-3-(2-bromoethoxy)quinoline
• 英文别名: 3-(2-bromoethoxy)quinolin-2-amine
• CAS: 143102-11-8
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: JIRSJMQRKZILSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-3-(2-bromoethoxy)quinoline 在 potassium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 以20%的产率得到morpholino<3,2-b>quinoline
  参考文献：
  名称：

  Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part 1.

  摘要：

  3-(2-Bromoethyltosylamino)quinoline 1-oxide (4) reacted with TsCl-NH4OH and TsCl-K2CO3 to afford the 2-aminoquinoline (5) and the 2-quinolinone (8). Cyclization of 5 and 8 under basic conditions gave the piperazino-quinoline (6) and the morpholino-quinoline (9). Similar reactions of 3-(2-bromoethoxy)quinoline 1-oxide (13) in the presence of TsCl gave also the 2-aminoquinoline (14) and the 2-hydroxyquinoline (16), but accompanied with fair amounts of by-products (15 and, 15 and 17). Cyclization of 14 and 16 gave the morpholino-quinoline (18) and the 1,4-dioxano-quinoline (19) in somewhat lower yields.

  DOI：

  10.3987/com-92-5999
• 作为产物：
  描述：

  3-(2-bromoethoxy)quinoline 在 ammonium hydroxide 、 对甲苯磺酰氯 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.17h， 生成 1-amino-3-(2-bromoethoxy)quinoline
  参考文献：
  名称：

  Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part 1.

  摘要：

  3-(2-Bromoethyltosylamino)quinoline 1-oxide (4) reacted with TsCl-NH4OH and TsCl-K2CO3 to afford the 2-aminoquinoline (5) and the 2-quinolinone (8). Cyclization of 5 and 8 under basic conditions gave the piperazino-quinoline (6) and the morpholino-quinoline (9). Similar reactions of 3-(2-bromoethoxy)quinoline 1-oxide (13) in the presence of TsCl gave also the 2-aminoquinoline (14) and the 2-hydroxyquinoline (16), but accompanied with fair amounts of by-products (15 and, 15 and 17). Cyclization of 14 and 16 gave the morpholino-quinoline (18) and the 1,4-dioxano-quinoline (19) in somewhat lower yields.

  DOI：

  10.3987/com-92-5999