9-methyl-3-(trimethylsilyl)-[1,2,3]triazolo[1,5-a]quinoline | 1165569-01-6

• 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: 9-methyl-3-(trimethylsilyl)-[1,2,3]triazolo[1,5-a]quinoline
• CAS: 1165569-01-6
• 化学式: C₁₄H₁₇N₃Si
• 分子量: 255.395
• InChiKey: NNIBVHMDUJSHOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-methyl-3-(trimethylsilyl)-[1,2,3]triazolo[1,5-a]quinoline 在 四丁基氟化铵 、 水 、 sodium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到9-methyl-[1,2,3]triazolo[1,5-a]quinoline
  参考文献：
  名称：

  The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

  摘要：

  New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.058
• 作为产物：
  描述：

  3-(trimethylsilyl)-[1,2,3]triazolo[1,5-a]quinoline 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以99%的产率得到9-methyl-3-(trimethylsilyl)-[1,2,3]triazolo[1,5-a]quinoline
  参考文献：
  名称：

  The deprotonative metalation of [1,2,3]triazolo[1,5-a]quinoline. Synthesis of 8-haloquinolin-2-carboxaldehydes

  摘要：

  New highly functionalized triazoloquinolines were synthesized by applying polar organometallic methods. Double metalation and functionalization provided 3,9-dihalogenated triazoloquinolines. Ring opening of the triazole with loss of nitrogen has been performed for the first time with 3,9-dihalogenated triazoloquinolines allowing the access toward 8-haloquinolin-2-carboxaldehydes under oxidant-free conditions. This approach demonstrates that the triazole ring can be used as protecting group of 2-quinolinecarboxaldehydes, activating the C9-position for lithiation and functionalization by triazole ring opening. 8-Haloquinoline-2-carbaldehydes become in this way readily available. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.058