ethyl 8-tert-butyl-7-hydroxy-9-oxo-8,9-dihydro-7H-phenaleno[1,9-ef]isoindole-7-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 8-tert-butyl-7-hydroxy-9-oxo-8,9-dihydro-7H-phenaleno[1,9-ef]isoindole-7-carboxylate
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: JYXDAVFTMKFEBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-(tert-butyl)pyrene-1-carboxamide 、 草酸二乙酯 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以75%的产率得到ethyl 8-tert-butyl-7-hydroxy-9-oxo-8,9-dihydro-7H-phenaleno[1,9-ef]isoindole-7-carboxylate
  参考文献：
  名称：

  Directed lithiation of a pyrene-1-carboxamide as a route to new pyrenyl fluorophores

  摘要：

  The lithiation of N-tert-butylpyrene-1-carboxamide with nBuLi-TMEDA in THF at -78 degrees C afforded, after quenching with chlorosilanes, the corresponding 2-(trialkylsilyl)pyrene-1-carboxamides. When DMF and diethyl oxalate were used as quenchers compounds having 8-tert-butyl-7-hydroxy-8,9-dihydro-7H-phenaleno-[1,9-ef]isoindole skeleton were obtained. The oxidation of compound having secondary OH group with Jones' reagent afforded 8-tert-butyl-7-hydroxy-8,9-dihydro-7H-phenaleno-[1,9-ef]isoindole-7,9(8H)dione. All of the synthesized compounds displayed fluorescence in solution (lambda(max) = 425-451 nm; Phi(F) = 15.1-40.8%) and in the solid state ((lambda(max) = 410-555 nm; Phi(F) = 6-40%). The silylated amides display in the solid state monomer emission whereas in the case of the of phenalenoisoindole derivatives the emitting species are pi-stacked aggregates. The formation of aggregates in the crystals of the latter compounds was confirmed by a single-crystal X-ray diffraction study. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.10.031