spiro[1'(5'-methylbenzocyclohexadien-4'-one)-1',61-methano[60]fullerene] | 350791-65-0

• 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: spiro[1'(5'-methylbenzocyclohexadien-4'-one)-1',61-methano[60]fullerene]
• CAS: 350791-65-0
• 化学式: C₇₁H₈O
• 分子量: 876.844
• InChiKey: XRBRPKWPRGLHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  72
• 可旋转键数：
  0
• 环数：
  35.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-Methyl-naphthochinon-(1,4)-diazid 、 足球烯 以 邻二氯苯 为溶剂， 反应 3.0h， 以17%的产率得到spiro[1'(5'-methylbenzocyclohexadien-4'-one)-1',61-methano[60]fullerene]
  参考文献：
  名称：

  Reductive Electrochemistry of Spiromethanofullerenes

  摘要：

  The synthesis and electrochemical properties of spiromethanofullerenes 1-6 are described. The syntheses were achieved via the diazomethane route, and the regioisomeric distribution of bis-adducts 3 was determined by H-1 NMR, UV-vis, and HPLC analysis. The electrochemistry of these compounds in dichloromethane exhibits, besides several reversible reductions, some irreversible waves. Reductive electrolysis of 1 and 3-5 in dichloromethane leads to the removal of the addend and thus to the formation of C-60 Reductive electrolysis of 1, 2 and 6 in dichloromethane leads to a different reaction, which we tentatively assign to a reaction with the solvent to form fullerene-CH2Cl products. Electrolyses in the less reactive solvent THF lead to adduct removal for 1 and 3-5. Interestingly, significant formation of bis-adducts from the corresponding monoadducts was observed for 4 and 5. These electrochemically induced reactions, namely addend removal, reaction with the solvent, and addend transfer are influenced by the structure of the addend and by the choice of solvent.

  DOI：

  10.1021/jo010297z

文献信息

• Reductive Electrochemistry of Spiromethanofullerenes
  作者：Marcel W. J. Beulen、José A. Rivera、M. Ángeles Herranz、Beatriz Illescas、Nazario Martín、Luis Echegoyen

  DOI：10.1021/jo010297z

  日期：2001.6.1

  The synthesis and electrochemical properties of spiromethanofullerenes 1-6 are described. The syntheses were achieved via the diazomethane route, and the regioisomeric distribution of bis-adducts 3 was determined by H-1 NMR, UV-vis, and HPLC analysis. The electrochemistry of these compounds in dichloromethane exhibits, besides several reversible reductions, some irreversible waves. Reductive electrolysis of 1 and 3-5 in dichloromethane leads to the removal of the addend and thus to the formation of C-60 Reductive electrolysis of 1, 2 and 6 in dichloromethane leads to a different reaction, which we tentatively assign to a reaction with the solvent to form fullerene-CH2Cl products. Electrolyses in the less reactive solvent THF lead to adduct removal for 1 and 3-5. Interestingly, significant formation of bis-adducts from the corresponding monoadducts was observed for 4 and 5. These electrochemically induced reactions, namely addend removal, reaction with the solvent, and addend transfer are influenced by the structure of the addend and by the choice of solvent.