(E,E)-2,5-bis[2-(5-nitrothien-2-yl)-1-(diethylamino)vinyl]thiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (E,E)-2,5-bis[2-(5-nitrothien-2-yl)-1-(diethylamino)vinyl]thiophene
• 英文别名: (E)-1-[5-[(E)-1-(diethylamino)-2-(5-nitrothiophen-2-yl)ethenyl]thiophen-2-yl]-N,N-diethyl-2-(5-nitrothiophen-2-yl)ethenamine
• 化学式: C₂₄H₂₈N₄O₄S₃
• 分子量: 532.709
• InChiKey: YNXIGEGRHUEHBP-MXWIWYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-溴-5-硝基噻吩 、 2,5-二(乙炔基)噻吩 、 二乙胺 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 (E,E)-2,5-bis[2-(5-nitrothien-2-yl)-1-(diethylamino)vinyl]thiophene 、 (E,Z)-2,5-bis[2-(5-nitrothien-2-yl)-1-(diethylamino)vinyl]thiophene
  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.