ethyl (4Z)-5-oxo-2-phenyl-4-[(2E)-3-phenylprop-2-en-1-ylidene]-4,5-dihydro-1H-pyrrole-3-carboxylate | 1393818-16-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (4Z)-5-oxo-2-phenyl-4-[(2E)-3-phenylprop-2-en-1-ylidene]-4,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 1393818-16-0
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: VXXRJHJCMGJVOI-PQGFFOKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• 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：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (4Z)-5-oxo-2-phenyl-4-[(2E)-3-phenylprop-2-en-1-ylidene]-4,5-dihydro-1H-pyrrole-3-carboxylate 在 potassium carbonate 作用下， 以 氘代二甲亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 170.33h， 生成 ethyl (4E)-1-methyl-5-oxo-2-phenyl-4-[(2E)-3-phenylprop-2-en-1-ylidene]-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Structure, Z/E photoisomerization and an effect of (phenylene-)vinylene conjugation extension on absorption and fluorescence of methylidene-pyrrolinones

  摘要：

  Six methylidene-pyrrolinones with a conjugation chain extended by vinylene and phenylene-vinylene groups were studied: five of them were synthesized for the first time. Their structures were estimated theoretically by density functional theory (DFT) and proved by X-ray diffraction techniques in two cases. Structural changes upon Z/E photoisomerization in solution were studied by a combination of H-1 NMR spectroscopy and DFT CIAO method. Both types of conjugation extension caused a bathochromic shift in absorption. Vinylene extension produced the compounds fluorescent in solution. N-methylated derivatives have shown solid-state fluorescence. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.04.061
• 作为产物：
  描述：

  反式肉桂醛 、 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 4.0h， 以56%的产率得到ethyl (4Z)-5-oxo-2-phenyl-4-[(2E)-3-phenylprop-2-en-1-ylidene]-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Structure, Z/E photoisomerization and an effect of (phenylene-)vinylene conjugation extension on absorption and fluorescence of methylidene-pyrrolinones

  摘要：

  Six methylidene-pyrrolinones with a conjugation chain extended by vinylene and phenylene-vinylene groups were studied: five of them were synthesized for the first time. Their structures were estimated theoretically by density functional theory (DFT) and proved by X-ray diffraction techniques in two cases. Structural changes upon Z/E photoisomerization in solution were studied by a combination of H-1 NMR spectroscopy and DFT CIAO method. Both types of conjugation extension caused a bathochromic shift in absorption. Vinylene extension produced the compounds fluorescent in solution. N-methylated derivatives have shown solid-state fluorescence. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.04.061