1,2,3,4-四氢吡嗪并[2,3-b]喹啉 | 143102-05-0

• 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
• 中文名称: 1,2,3,4-四氢吡嗪并[2,3-b]喹啉
• 中文别名: 锇杂锡
• 英文名称: piperazino<2,3-b>quinoline
• 英文别名: 1,2,3,4-Tetrahydropyrazino[2,3-b]quinoline
• CAS: 143102-05-0
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: KHXVULBTQYHKIV-UHFFFAOYSA-N

物化性质

• 沸点：
  429.5±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-N-tosylaminoquinoline 在 ammonium hydroxide 、 硫酸 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酰氯 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 13.0h， 生成 1,2,3,4-四氢吡嗪并[2,3-b]喹啉
  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

文献信息

• Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part 1.
  作者：Yutaka Miura、Sakae Takaku、Yasuo Fujimura、Masatomo Hamana

  DOI：10.3987/com-92-5999

  日期：——

  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.