1-(9-butyl-9H-carbazol-3-yl)-3-(2-thienyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(9-butyl-9H-carbazol-3-yl)-3-(2-thienyl)prop-2-en-1-one
• 英文别名: 1-(9-Butyl-9h-carbazol-3-yl)-3-(2-thienyl)prop-2-en-1-one；1-(9-butylcarbazol-3-yl)-3-thiophen-2-ylprop-2-en-1-one
• 化学式: C₂₃H₂₁NOS
• 分子量: 359.492
• InChiKey: BQDMSYIBPJYNDC-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：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙酰基吡啶 、 1-(9-butyl-9H-carbazol-3-yl)-3-(2-thienyl)prop-2-en-1-one 在 sodium hydroxide 作用下， 反应 1.5h， 以76%的产率得到
  参考文献：
  名称：

  A facile and highly efficient green synthesis of carbazole derivatives containing a six-membered ring

  摘要：

  A facile and efficient green protocol for the synthesis of carbazole derivatives containing a six-membered ring, via an aldol condensation and solvent-free Michael addition reaction, has been developed. The compounds were characterized by H-1 NMR, C-13 NMR, IR, ESI-MS and HR-MS spectroscopic techniques and also, for one example, by X-ray crystallography. The cyclohexyl unit was introduced into the carbazole derivatives and utilized as a sterically demanding group for the purpose of increasing the non-planarity of the carbazole derivatives and reducing self-quenching, leading to improved optical and electronic properties. The influence of solvent polarity on the ultraviolet absorption and fluorescence characteristics was observed and investigated. The majority of the carbazole derivatives have high fluorescence quantum yields in dichloromethane, ethanol, acetonitrile and DMF. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.009
• 作为产物：
  描述：

  N-正丁基咔唑 在 四氯化锡 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-(9-butyl-9H-carbazol-3-yl)-3-(2-thienyl)prop-2-en-1-one
  参考文献：
  名称：

  New carbazole-containing chalcones and pyrimidines based thereon: Synthesis and electrochemical study

  摘要：

  Condensations of aromatic carbo- and heterocyclic ketones and aldehydes in methanol gave new chalcones containing carbazole fragments, 1,3-diaryl(9-R-9H-carbazol-3-yl)prop-2-en-1-ones. Some of the synthesized chalcones reacted with guanidine sulfate to produce 2-amino-4,6-diarylpyrimidines that are promising materials for the design of light emitting diodes. Study on electrochemical polymerization of both chalcones and pyrimidines derived therefrom showed that almost all the examined substrates give rise to stable colored conjugated polymer films on the surface of working electrode under conditions of cyclic voltammetry.

  DOI：

  10.1134/s1070428011040117

文献信息

• New carbazole-containing chalcones and pyrimidines based thereon: Synthesis and electrochemical study
  作者：R. V. Syutkin、G. G. Abashev、E. V. Shklyaeva、P. G. Kudryavtsev

  DOI：10.1134/s1070428011040117

  日期：2011.4

  Condensations of aromatic carbo- and heterocyclic ketones and aldehydes in methanol gave new chalcones containing carbazole fragments, 1,3-diaryl(9-R-9H-carbazol-3-yl)prop-2-en-1-ones. Some of the synthesized chalcones reacted with guanidine sulfate to produce 2-amino-4,6-diarylpyrimidines that are promising materials for the design of light emitting diodes. Study on electrochemical polymerization of both chalcones and pyrimidines derived therefrom showed that almost all the examined substrates give rise to stable colored conjugated polymer films on the surface of working electrode under conditions of cyclic voltammetry.
• A facile and highly efficient green synthesis of carbazole derivatives containing a six-membered ring
  作者：Haowei Wang、Yu Chen、Wenbo Ye、Jingkun Xu、Daofu Liu、Jiaxiang Yang、Lin Kong、Hongping Zhou、Yupeng Tian、Xutang Tao

  DOI：10.1016/j.dyepig.2012.11.009

  日期：2013.3

  A facile and efficient green protocol for the synthesis of carbazole derivatives containing a six-membered ring, via an aldol condensation and solvent-free Michael addition reaction, has been developed. The compounds were characterized by H-1 NMR, C-13 NMR, IR, ESI-MS and HR-MS spectroscopic techniques and also, for one example, by X-ray crystallography. The cyclohexyl unit was introduced into the carbazole derivatives and utilized as a sterically demanding group for the purpose of increasing the non-planarity of the carbazole derivatives and reducing self-quenching, leading to improved optical and electronic properties. The influence of solvent polarity on the ultraviolet absorption and fluorescence characteristics was observed and investigated. The majority of the carbazole derivatives have high fluorescence quantum yields in dichloromethane, ethanol, acetonitrile and DMF. (C) 2012 Elsevier Ltd. All rights reserved.