1-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-quinolin-3-yl}-ethanol | 852435-20-2

• 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-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-quinolin-3-yl}-ethanol
• CAS: 852435-20-2
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: YYZVTECOQBMJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.58
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-quinolin-3-yl}-ethanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以81%的产率得到1-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-quinolin-3-yl}-ethanone
  参考文献：
  名称：

  An Efficient and Simple Aminobenzannulation Reaction:  Pyrrolidine as a Trigger for the Synthesis of 1-Amino-acridines

  摘要：

  A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 angstrom molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al2O3 or PtCl2 catalysis was necessary.

  DOI：

  10.1021/ol050380z
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 1-{2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-quinolin-3-yl}-ethanol
  参考文献：
  名称：

  An Efficient and Simple Aminobenzannulation Reaction:  Pyrrolidine as a Trigger for the Synthesis of 1-Amino-acridines

  摘要：

  A new aminobenzannulation methodology has been developed and applied successfully to the synthesis of 1-amino-acridines. The key and last step goes through an enamine intermediate that was detected in some cases. When pyrrolidine and powdered 4 angstrom molecular sieves were used, the enamine synthesis and the aminobenzannulation step took place subsequently, whereas for other secondary amines, neutral Al2O3 or PtCl2 catalysis was necessary.

  DOI：

  10.1021/ol050380z