(E)-4-[2-(5-nitropyrid-2-yl)-1-phenylvinyl]morpholine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-[2-(5-nitropyrid-2-yl)-1-phenylvinyl]morpholine
• 英文别名: 4-[(E)-2-(5-nitropyridin-2-yl)-1-phenylethenyl]morpholine
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: IBMDSIUIJQEIKG-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吗啉 、 2-溴-5-硝基吡啶 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 作用下， 以 四氢呋喃 、 三乙胺 、 甲醇 为溶剂， 反应 6.0h， 生成 (Z)-4-[2-(5-nitropyrid-2-yl)-1-phenylvinyl]morpholine 、 (E)-4-[2-(5-nitropyrid-2-yl)-1-phenylvinyl]morpholine
  参考文献：
  名称：

  Facile One-Pot Coupling−Aminovinylation Approach to Push−Pull Chromophores:  Alkyne Activation by Sonogashira Coupling

  摘要：

  A straightforward coupling-aminovinylation sequence of terminal alkynes 1, electron-deficient heteroaryl halides 2, and secondary amines 4 furnishes highly solvochromic push-pull chromophores 5 in good yields. Semiempirical calculations (PM3) suggest that the aminovinylation proceeds in a stepwise fashion through a zwitterionic intermediate with a final rate-determining intramolecular protonation. Crucial parameters for the success of the amine addition are the relative LUMO energies and the charge distribution at the beta-alkynyl carbon atom.

  DOI：

  10.1021/jo026470o

文献信息

• Facile One-Pot Coupling−Aminovinylation Approach to Push−Pull Chromophores:  Alkyne Activation by Sonogashira Coupling
  作者：Alexei S. Karpov、Frank Rominger、Thomas J. J. Müller

  DOI：10.1021/jo026470o

  日期：2003.2.1

  A straightforward coupling-aminovinylation sequence of terminal alkynes 1, electron-deficient heteroaryl halides 2, and secondary amines 4 furnishes highly solvochromic push-pull chromophores 5 in good yields. Semiempirical calculations (PM3) suggest that the aminovinylation proceeds in a stepwise fashion through a zwitterionic intermediate with a final rate-determining intramolecular protonation. Crucial parameters for the success of the amine addition are the relative LUMO energies and the charge distribution at the beta-alkynyl carbon atom.