4,4'-di(N-Boc-amino)diphenyldiacetylene | 1198566-41-4

• 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: 4,4'-di(N-Boc-amino)diphenyldiacetylene
• CAS: 1198566-41-4
• 化学式: C₂₆H₂₈N₂O₄
• 分子量: 432.519
• InChiKey: AGSPHPYYKHHFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,4'-di(N-Boc-amino)diphenyldiacetylene 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 42.0h， 生成 4,4’-(丁-1,3-二炔-1,4-二基)二苯胺
  参考文献：
  名称：

  Electronic properties of hyperbranched compounds derived by pyrrole

  摘要：

  The electronic structure of hyperbranched polymers obtained from para-diaminodiphenyldiacetylenes as AB(2) type monomers by one-step polymerization is studied using DFT calculations. Five generations are modelled with optimization at each step. As the molecule grows it shows a helical shape conserving the C2 symmetry with wing like fragments covering the backbone. There is accidental degeneracy of the HOMO with the HOMO-1 and of the HOMO-2 with the HOMO-3. The LUMO is always located at the backbone and the HOMO set at the dianyline-pyrrole fragment. The HOMO-LUMO gap decreases as the molecule grows. Conductivity measurements as well as microscopy studies of para-hyperbranched polymer were carried out. Conductivity measurements as a function of temperature show semiconductor behavior. Optical microscopy reveals a macroscopic crystalline structure of this hyperbranched polymer. (c) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.06.031
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 6.0h， 生成 4,4'-di(N-Boc-amino)diphenyldiacetylene
  参考文献：
  名称：

  Electronic properties of hyperbranched compounds derived by pyrrole

  摘要：

  The electronic structure of hyperbranched polymers obtained from para-diaminodiphenyldiacetylenes as AB(2) type monomers by one-step polymerization is studied using DFT calculations. Five generations are modelled with optimization at each step. As the molecule grows it shows a helical shape conserving the C2 symmetry with wing like fragments covering the backbone. There is accidental degeneracy of the HOMO with the HOMO-1 and of the HOMO-2 with the HOMO-3. The LUMO is always located at the backbone and the HOMO set at the dianyline-pyrrole fragment. The HOMO-LUMO gap decreases as the molecule grows. Conductivity measurements as well as microscopy studies of para-hyperbranched polymer were carried out. Conductivity measurements as a function of temperature show semiconductor behavior. Optical microscopy reveals a macroscopic crystalline structure of this hyperbranched polymer. (c) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.06.031

文献信息

• Synthesis of 1,2,5-substituted pyrrole derivatives by a modification of the Reisch-Schulte reaction
  作者：Marco A. Almaraz-Girón、Carla Aguilar-Lugo、Giovanna Angélica Vázquez-Hernández、Sergei Fomine、Roberto Salcedo、Larissa Alexandrova、Lioudmila Fomina

  DOI：10.1016/j.molstruc.2023.137232

  日期：2024.3

  A synthesis method was developed for the formation of several 1,2,5-substituted pyrrole derivatives and were characterized by NMR, IR, UV-Vis spectroscopies and HRMS. This method involves adding aniline derivatives to a di-alkyne, catalyzed by Cu(I) and is carried out under modified Reisch-Schulte protocol by adding N,N,N′,N′-tetramethylethylenediamine (TMEDA). Notably, the reaction does not proceed

  开发了几种 1,2,5-取代吡咯衍生物的合成方法，并通过 NMR、IR、UV-Vis 光谱和 HRMS 进行了表征。该方法涉及在 Cu(I) 催化下将苯胺衍生物添加到二炔中，并在改进的 Reisch-Schulte 方案下通过添加N,N,N ', N '-四甲基乙二胺 (TMEDA) 进行。值得注意的是，在没有 TMEDA 的情况下反应不会进行。合成吡咯的产率范围从定量到可接受的范围。一般来说，反应产率与理论计算得到的苯胺试剂的全局亲核性（GN）有很好的相关性；除了对甲氧基苯胺（GN 值最大的分子）之外，更多的亲核苯胺会导致更高的产率。提出了观察到的效应的机制解释。此外，实验研究和理论模拟表明，新型吡咯分子具有半导体特性，因为它们的带隙能量（Eg）位于有机半导体的典型范围内。据观察，吸电子基团的存在导致Eg值显着降低。