2-cyclohexyl-5,7-dimethoxy-4-phenylquinoline

• 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: 2-cyclohexyl-5,7-dimethoxy-4-phenylquinoline
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: SKIUHMXXDGBAPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3,5-dimethoxyphenyl)cyclohexanecarboxamide 、 1-苯基-1-三甲基硅氧乙烯 在 2-氯吡啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以62%的产率得到2-cyclohexyl-5,7-dimethoxy-4-phenylquinoline
  参考文献：
  名称：

  Direct Synthesis of Pyridine Derivatives

  摘要：

  We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyridine and quinoline derivatives, respectively. The process involves amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by pi-nucleophile addition to the activated intermediate and annulation. Compatibility of this chemistry with sensitive N-vinyl amides, epimerizable substrates, and a variety of functional groups is noteworthy.

  DOI：

  10.1021/ja073912a

文献信息

• Direct Synthesis of Pyridine Derivatives
  作者：Mohammad Movassaghi、Matthew D. Hill、Omar K. Ahmad

  DOI：10.1021/ja073912a

  日期：2007.8.1

  We describe a single-step conversion of various N-vinyl and N-aryl amides to the corresponding pyridine and quinoline derivatives, respectively. The process involves amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by pi-nucleophile addition to the activated intermediate and annulation. Compatibility of this chemistry with sensitive N-vinyl amides, epimerizable substrates, and a variety of functional groups is noteworthy.