1-(3-(ω-N-Histaminocarbonyl)propyl)-1-phenyl<6.6>C61

• 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: 1-(3-(ω-N-Histaminocarbonyl)propyl)-1-phenyl<6.6>C61
• 英文别名: 1-[3-(ω-N-Histaminocarbonyl)propyl]-1-phenyl[6.6]C61
• 化学式: C₇₆H₁₉N₃O
• 分子量: 990.006
• InChiKey: HPHKROILKXHYCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  80
• 可旋转键数：
  8
• 环数：
  35.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  组胺 、 1-(3-(Chlorocarbonyl)propyl)-1-phenyl<6.6>C61 在 吡啶 作用下， 反应 18.0h， 以68%的产率得到1-(3-(ω-N-Histaminocarbonyl)propyl)-1-phenyl<6.6>C61
  参考文献：
  名称：

  Preparation and Characterization of Fulleroid and Methanofullerene Derivatives

  摘要：

  We describe the synthesis and complete characterization of soluble derivatives of C-60 for applications to physics and biology. The goal of the strategy was to have a ''modular'' approach in order to be able to easily vary a functional group attached indirectly to the cluster. The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy). The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes. An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques. This problem was solved by the use of MALDIMS. The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives. Both isomeric forms ([5,6], fulleroid and [6,6], methanofullerene) of the C-61 clusters were prepared. The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively. The fulleroid and methano-fullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.

  DOI：

  10.1021/jo00108a012

文献信息

• Preparation and Characterization of Fulleroid and Methanofullerene Derivatives
  作者：Jan C. Hummelen、Brian W. Knight、F. LePeq、Fred Wudl、Jie Yao、Charles L. Wilkins

  DOI：10.1021/jo00108a012

  日期：1995.2

  We describe the synthesis and complete characterization of soluble derivatives of C-60 for applications to physics and biology. The goal of the strategy was to have a ''modular'' approach in order to be able to easily vary a functional group attached indirectly to the cluster. The functionality could be hydrophilic (e.g., histamide) or hydrophobic (e.g., cholestanoxy). The former was prepared for biological studies and the latter for photophysical studies toward improvement of photoinduced electron transfer efficiencies in the fabrication of photodetectors and photodiodes. An important intermediate, a carboxylic acid, was found to be recalcitrant to characterization by the usual mass spectroscopic and elemental analysis techniques. This problem was solved by the use of MALDIMS. The carboxylic acid was easily converted to the key intermediate acid chloride, which in turn was convertible to a large variety of derivatives. Both isomeric forms ([5,6], fulleroid and [6,6], methanofullerene) of the C-61 clusters were prepared. The fulleroid formation could have given rise to a 50:50 mixture of phenyl-over-former pentagon phenyl-over-former hexagon isomers but, remarkably, afforded a 95:5 mixture of these isomers, respectively. The fulleroid and methano-fullerene gave different cyclic voltammograms, with the former being reduced at 34 mV more positive potential than the latter.