ethyl (4Z)-5-oxo-2-phenyl-4-(2,2'-bithiophen-5-ylmethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylate | 1436999-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: ethyl (4Z)-5-oxo-2-phenyl-4-(2,2'-bithiophen-5-ylmethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 1436999-02-8
• 化学式: C₂₂H₁₇NO₃S₂
• 分子量: 407.514
• InChiKey: KJWXIUFUBKUYCQ-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (4Z)-5-oxo-2-phenyl-4-(2,2'-bithiophen-5-ylmethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylate 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 以92%的产率得到ethyl (4Z)-4-(2,2'-bithiophen-5-ylmethylidene)-1-methyl-5-oxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Structure, absorption and fluorescence of (bi)thiophene substituted methylidene-pyrrolinones

  摘要：

  Four thiophene and bithiophene substituted methylidene-pyrrolinones were synthesized and their absorption and fluorescence properties were compared with previously reported behavior of their phenyl and biphenyl substituted analogues. Their structures were estimated theoretically by density functional theory (DFT) and proved by X-ray diffraction in two cases. Thiophene derivatives show a considerable bathochromic shifts in absorption with respect to phenyl analogues, in accordance with theoretical predictions based on time dependent DFT. Conjugation extension caused a bathochromic shift in absorption, too. All compounds show fluorescence in low temperature solvent glass, while only one bithiophene substituted derivative fluoresce weakly in room temperature solution. Three of four N-methylated derivatives show strong yellow, orange and red solid-state fluorescence. An ability of solid-state fluorescence was correlated with nearest neighbor out-of-plane interactions in crystal. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.03.055
• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 、 2-氧代-5-苯基-1,3-二氢吡咯-4-羧酸乙酯 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以95%的产率得到ethyl (4Z)-5-oxo-2-phenyl-4-(2,2'-bithiophen-5-ylmethylidene)-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Structure, absorption and fluorescence of (bi)thiophene substituted methylidene-pyrrolinones

  摘要：

  Four thiophene and bithiophene substituted methylidene-pyrrolinones were synthesized and their absorption and fluorescence properties were compared with previously reported behavior of their phenyl and biphenyl substituted analogues. Their structures were estimated theoretically by density functional theory (DFT) and proved by X-ray diffraction in two cases. Thiophene derivatives show a considerable bathochromic shifts in absorption with respect to phenyl analogues, in accordance with theoretical predictions based on time dependent DFT. Conjugation extension caused a bathochromic shift in absorption, too. All compounds show fluorescence in low temperature solvent glass, while only one bithiophene substituted derivative fluoresce weakly in room temperature solution. Three of four N-methylated derivatives show strong yellow, orange and red solid-state fluorescence. An ability of solid-state fluorescence was correlated with nearest neighbor out-of-plane interactions in crystal. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.03.055