61-ethoxy-61-(ethoxycarbonyl)1,2-dihydro-1,2-methano[60]fullerene

• 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: 61-ethoxy-61-(ethoxycarbonyl)1,2-dihydro-1,2-methano[60]fullerene
• 化学式: C₆₆H₁₀O₃
• 分子量: 850.804
• InChiKey: SERRECXYCXXIHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  69
• 可旋转键数：
  5
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2-(6161,62,62-tetraethoxycyclobutano)dihydro[60]fullerene 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到61-ethoxy-61-(ethoxycarbonyl)1,2-dihydro-1,2-methano[60]fullerene
  参考文献：
  名称：

  [2 + 2] Cycloaddition of Fullerenes with Electron-Rich Alkenes and Alkynes

  摘要：

  Photochemical [2 + 2] cycle addition of C-60 with N,N-diethyl-4-methyl-3-penten-1-yn-1-amine (1) afforded the stable C-60-fused cyclobutenamine 2 which underwent self-sensitized photooxidation to dihydrofullerenone amide 4 in high yield. Fullerenes C-60 and C-70 react thermally with tetraalkoxyethylenes to give dihydrofullerene cyclobutanediketals, which undergo a clean cyclo-reversion to fullerenes on irradiation with visible or UV light. Attempted hydrolysis of the ketals was unsuccessful, but treatment of 1,2-(6161,62,62-tetraethoxycyclobutano)dihydro[60]fullerene (8) with TMSI gave ring-contracted product 11 (by cleavage of the C-C bond to the fullerene fragment) along with reduction product 12.

  DOI：

  10.1021/jo9602231

文献信息

• [2 + 2] Cycloaddition of Fullerenes with Electron-Rich Alkenes and Alkynes
  作者：Xiaojun Zhang、Andrew Fan、Christopher S. Foote

  DOI：10.1021/jo9602231

  日期：1996.1.1

  Photochemical [2 + 2] cycle addition of C-60 with N,N-diethyl-4-methyl-3-penten-1-yn-1-amine (1) afforded the stable C-60-fused cyclobutenamine 2 which underwent self-sensitized photooxidation to dihydrofullerenone amide 4 in high yield. Fullerenes C-60 and C-70 react thermally with tetraalkoxyethylenes to give dihydrofullerene cyclobutanediketals, which undergo a clean cyclo-reversion to fullerenes on irradiation with visible or UV light. Attempted hydrolysis of the ketals was unsuccessful, but treatment of 1,2-(6161,62,62-tetraethoxycyclobutano)dihydro[60]fullerene (8) with TMSI gave ring-contracted product 11 (by cleavage of the C-C bond to the fullerene fragment) along with reduction product 12.