1-(4-dimethylaminophenyl)-2-(5H-phenanthridine-6-ylidene)-ethanone | 938155-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(4-dimethylaminophenyl)-2-(5H-phenanthridine-6-ylidene)-ethanone
• 英文别名: 6-[4-(Dimethylamino)phenacyl]phenanthridine；1-[4-(dimethylamino)phenyl]-2-phenanthridin-6-ylethanone
• CAS: 938155-11-4
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: YXUDOLSUGNSQGS-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  561.7±35.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-甲基菲啶 、 4-二甲氨基苯甲酸乙酯 在 苯基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以10.5%的产率得到1-(4-dimethylaminophenyl)-2-(5H-phenanthridine-6-ylidene)-ethanone
  参考文献：
  名称：

  π-电子离域对互变异构平衡的影响 - 苯并环化 2-苯基吡啶

  摘要：

  大多数苯并环化的 2-甲基吡啶与苯基锂和取代的苯甲酸烷基酯反应生成相应的 2-苯甲酰基吡啶。在这些条件下，3-甲基异喹啉转化为 2-苯甲酰基-3-甲基-1-苯基-1,2-二氢异喹啉，但用异丙基环己基氨基锂替代苯基锂对生产 3-苯甲酰基异喹啉有效。除了某些取代的 6-苯甲酰基菲啶外，氯仿溶液中苯并环化 2-苯甲酰基吡啶的互变异构混合物总是含有酮亚胺形式。 (Z)-2-(2-羟基-2-苯基乙烯基)吡啶（烯亚胺）形式也有助于吡啶环没有苯并环化，或者如果这种环化在 4,5 位。另一方面，(Z)-2-benzoylmethylene-1, 如果吡啶环在 3,4 或 5,6 位或这两个位置被苯环化，则 2-二氢吡啶（烯胺酮）形式与酮亚胺互变异构体处于平衡状态。除了 π 电子离域的有效性外，还应考虑其他影响，例如分子内氢键的强度，以推断互变异构的偏好。发现强给电子取代基可稳定每个系列中的酮亚胺形式。(©

  DOI：

  10.1002/ejoc.200500840

文献信息

• Solvatochromic, spectroscopic and DFT studies of a novel synthesized dye: l-(4-Dimethylaminophenyl)-2-(5H-phenanthridine-6-ylidene)-ethanone (6-KMPT)
  作者：Ali Hassanzadeh、Hossein Loghmani-Khouzani、Majid M. Sadeghi、Hossein Mehrabi

  DOI：10.1016/j.saa.2006.06.036

  日期：2007.5

  A novel solvatochromic1-(4-dimethylaminophenyt)-2-(5H-phenanthridine-6-ylidene)-ethanone (6-KMPT) dye was synthesized and characterized by means of NMR, IR, mass spectroscopies. Also, it was studied using UV-vis and fluorescence spectroscopic methods in a broad range of solvents. UV-vis results showed that increasing 6-KMPT concentration dose not cause molecular aggregation in chloroform. Varying the temperature in the range from 25 to 55 degrees C dose not have a significant effect on the characteristics bands of the molecule. However, in the presence of surfactant SDS the UV-vis spectrum undergoes drastic alteration. This phenomenon is related to the removal of hydrogen atom from nitrogen atom of phenanthridine moiety. Fluorescence spectroscopic results showed that 6-KMPT has an appreciable fluorescence quantum yield. The effect of excitation wavelength, concentration of 6-KMPT, concentration of oxygen and surfactants (SDS, C(16)TAB, CPC, Brij-35) were studied. Further results showed that the fluorescent behavior of 6-KMPT can be attributed to planarity induced by intramolecular hydrogen bonding which can in turn be destroyed by anionic surfactant SDS. Results showed that oxygen and SDS can be operate as fluorescence quencher compounds for 6-KMPT and Stern-Volmer plot showed a straight line. Fluorescence polarization and anisotropy of 6-KMPT in chloroform strongly depend on concentration. The 6-KMPT exhibits solvent-induced spectral band shifts. By using Lippert equation, the change of dipole moment of 6-KMPT molecule upon excitation was estimated as 6.39 D. Furthermore, absorption, fluorescence emission, Stokes shift values and fluorescence quantum yield (OF) of 6-KMPT in different solvents of polarity were determined. Maximum OF value of 0.372 for 6-KMPT molecule was found in ethanol solvent with a Stokes shift of 2446.8 cm(-1). The results of DFT calculations showed that tautomer 2c (enol) energetically is more stable than tautomer 2b (keto) in gas phase whereas it was vice versa in CHCI3. (c) 2006 Elsevier B.V. All rights reserved.