dimethyl 1,4-dihydro-2,6-dimethyl-4-(9-phenanthryl)-3,5-dicarboxylate | 392722-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: dimethyl 1,4-dihydro-2,6-dimethyl-4-(9-phenanthryl)-3,5-dicarboxylate
• 英文别名: Dimethyl 2,6-dimethyl-4-phenanthren-9-yl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 392722-19-9
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: DDIVWFHNFPQGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 、 9-甲醛菲 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 4.5h， 以4%的产率得到dimethyl 1,4-dihydro-2,6-dimethyl-4-(9-phenanthryl)-3,5-dicarboxylate
  参考文献：
  名称：

  Photoinduced Electron and Energy Transfer in Aryldihydropyridines

  摘要：

  Dimethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates (Hantzsch DHPs) fluoresce weakly in fluid solution. However, these compounds exhibit an efficient fluorescence both in a viscous medium (glycerin) at room temperature and in a glassy matrix at 77 K (but no phosphorescence, since ISC is negligible). DHPs bearing an aryl roup in position 4 have been synthesized. These contain two different pi systems separated by an sp(3) carbon (DHP-Ar dyads). The occurrence of energy and electron transfer processes between the chromophores is investigated through luminescence measurements. In particular, when Ar-3 emits at a slow rate (e.g., Ar = phenanthryl) or not at all (Ar = nitrophenyl) the intradyad forward/backward electron transfer sequence offers a path for arriving at the DHP-localized triplet and the corresponding phosphorescence is observed. When Ar-3 emits at a faster rate (Ar = acylphenyl), the phosphorescence from either of the two localized triplets, Ar-3 or (DHP)-D-3, can be observed depending on lambda(exc.) When the aryl group has a triplet energy lower than that of (DHP)-D-3, this functions as emitting (4-cyano-l-naphthyl) or nonemitting (MeO2CCH=CHC6H4) energy sink. The results document the possibility of building tailor-made Hantzsch aryldihydropyridines as versatile photoactivated dyads.

  DOI：

  10.1021/jo9010816

文献信息

• Photoinduced Electron and Energy Transfer in Aryldihydropyridines
  作者：Angel J. Jimenez、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1021/jo9010816

  日期：2009.9.4

  Dimethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates (Hantzsch DHPs) fluoresce weakly in fluid solution. However, these compounds exhibit an efficient fluorescence both in a viscous medium (glycerin) at room temperature and in a glassy matrix at 77 K (but no phosphorescence, since ISC is negligible). DHPs bearing an aryl roup in position 4 have been synthesized. These contain two different pi systems separated by an sp(3) carbon (DHP-Ar dyads). The occurrence of energy and electron transfer processes between the chromophores is investigated through luminescence measurements. In particular, when Ar-3 emits at a slow rate (e.g., Ar = phenanthryl) or not at all (Ar = nitrophenyl) the intradyad forward/backward electron transfer sequence offers a path for arriving at the DHP-localized triplet and the corresponding phosphorescence is observed. When Ar-3 emits at a faster rate (Ar = acylphenyl), the phosphorescence from either of the two localized triplets, Ar-3 or (DHP)-D-3, can be observed depending on lambda(exc.) When the aryl group has a triplet energy lower than that of (DHP)-D-3, this functions as emitting (4-cyano-l-naphthyl) or nonemitting (MeO2CCH=CHC6H4) energy sink. The results document the possibility of building tailor-made Hantzsch aryldihydropyridines as versatile photoactivated dyads.