1-ethyl-2,3,4,5-tetraphenyl-1H-pyrrole | 53309-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-ethyl-2,3,4,5-tetraphenyl-1H-pyrrole
• 英文别名: 1-Ethyl-2,3,4,5-tetraphenylpyrrole
• CAS: 53309-76-5
• 化学式: C₃₀H₂₅N
• 分子量: 399.535
• InChiKey: SFHGVTVQRBCLGH-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  459.1±34.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-ethyl-2,3,4,5-tetraphenyl-1H-pyrrole 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 以18%的产率得到3,6,12,15-tetrachloro-9-ethyl-tetrabenzo[a,c,g,i]carbazole
  参考文献：
  名称：

  四苯基吡咯的光化学和氧化环化

  摘要：

  四苯基吡咯的光化学和氧化环脱氢反应以互补的方式作用于N-乙基和N-苄基衍生物的环化。在前者的情况下，从固体FeCl 3的环化中分离出双环化产物，而后者在辐照时给出了重排的3 H-吡咯。

  DOI：

  10.1039/c7ob02537h
• 作为产物：
  描述：

  1,2,3,4-四苯基-1,4-丁烷二酮 在 乙酸铵 、 sodium hydride 、 溶剂黄146 作用下， 以 正己烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 28.0h， 生成 1-ethyl-2,3,4,5-tetraphenyl-1H-pyrrole
  参考文献：
  名称：

  Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes

  摘要：

  In this work, a series of aryl-substituted pyrrole analogues were synthesized. These pyrrole analogues emit violet to blue light. Fluorescence and amorphous glassy properties of these pyrrole analogues were induced by manipulating the peripheral aryl groups. These crowded peripheral aryl groups would effectively prevent the fluorophores from aggregation, resulting in higher quantum efficiency and a stable emission spectrum in the solid state. One of the aryl-substituted pyrrole analogues, namely NPANPy can be used as hole-transporting material or hole-transporting/emitting material. The devices would emit blue light when the fluorophore NPANPy acts as the hole-transporting/ emitting material. Their CIE coordinate is around (0.16, 0.14), whereas the maximum brightness can reach 4300-5000 cd m(-2). Apart from that, when the fluorophore was used only as the hole-transporting material, better device performances, especially in low current density, were found, as compared with the standard device. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.032

文献信息

• Palladium(II)-Catalyzed [2+2+1] Annulation of Alkynes and Hydroxylamines: A Rodox-Neutral Approach to Fully Substituted Pyrroles
  作者：Jiaxing Bai、Nengni Xu、Hui Wang、Xinjun Luan

  DOI：10.1021/acs.orglett.2c01925

  日期：2022.7.22

  A palladium-catalyzed [2+2+1] annulation of alkynes and hydroxylamines has been developed for the rapid construction of fully substituted pyrroles. This transformation involves sequential nucleophilic-addition of hydroxylamine to alkyne, alkyne migratory insertion, and synergistic demetallization cyclization, which provides a redox-neutral annulation approach to pyrrole derivatives. Moreover, the strategy

  已经开发了一种钯催化的炔烃和羟胺的 [2+2+1] 环化，用于快速构建完全取代的吡咯。这种转变包括羟胺与炔烃的顺序亲核加成、炔烃迁移插入和协同脱金属环化，这为吡咯衍生物提供了一种氧化还原中性环化方法。此外，该策略能够通过改变芳基取代基来改变吡咯产物的光物理性质，从而导致开发出N-官能化四芳基吡咯作为新的荧光团。
• Acid-Promoted Cross-Dehydrative Aromatization for the Synthesis of Tetraaryl-Substituted Pyrroles
  作者：Xudong Wu、Ke Li、Siyuan Wang、Chao Liu、Aiwen Lei

  DOI：10.1021/acs.orglett.5b03240

  日期：2016.1.4

  Tetraaryl-substituted pyrroles are one important class of luminophores. In this work, an acid-promoted cross-dehydrative aromatization between benzoin and deoxybenzion was developed. This transformation provides an efficient and straightforward path for the synthesis of various aryl group substituted tetraarylpyrroles. Good to excellent yields were obtained through the easy operation with acetic acid and ammonium acetate.
• Fehrlin, Chemische Berichte, 1889, vol. 22, p. 555
  作者：Fehrlin

  DOI：——

  日期：——
• Boehm, Stanislav; Slavik, Hanus; Kuthan, Josef, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 1, p. 200 - 205
  作者：Boehm, Stanislav、Slavik, Hanus、Kuthan, Josef

  DOI：——

  日期：——