61,61-bis(diisopropoxyphosphoryl)methano[60]fullerene | 458523-76-7

• 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: 61,61-bis(diisopropoxyphosphoryl)methano[60]fullerene
• 英文别名: bis(diisopropoxyphosphoryl)methanofullerene C60；bis(diisopropoxyphosphoryl)methano[60]fullerene
• CAS: 458523-76-7
• 化学式: C₇₃H₂₈O₆P₂
• 分子量: 1062.97
• InChiKey: PABYXOSDGJNATR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.09
• 重原子数：
  81.0
• 可旋转键数：
  10.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  61,61-bis(diisopropoxyphosphoryl)methano[60]fullerene 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 生成 足球烯
  参考文献：
  名称：

  摘要：

  Four steps of reduction were detected for bis(diethoxyphosphoryl)- and bis(diisopropoxyphosphoryl)methano[60]fullerenes (1, 2) and bis(dietlioxyphosphoryl)methano[70]fullerene (3) by cyclic voltammetry in the o-dichlorobenzene-DMF (3 : 1, v/v)/Bu4NBF4 (0.1 mol L-1) system on a glass-carbon electrode. At the first step the reversible transfer of one electron affords stable radical anions 1 and 2 (g = 1.9999, DeltaH = 1.9 G). When two electrons per molecule are transferred, the methano fragment is rapidly eliminated (retro-Bingel reaction). This process involves the step-by-step cleavage of two C-C bonds of exo-carbon with the fullerene shell in combination with the stepwise transfer of other two electrons and a proton to form finally the carbanion of the methano fragment and fullerene dianion. For all Studied compounds, the elimination rate is much higher than that for bis(alkoxycarbonyl)-and dialkoxyphosphoryl(alkoxycarbonyl)methano[60]fullerenes, which makes it possible to propose bisphosphorylmethane groups as protective in synthesis of new fullerene derivatives.

  DOI：

  10.1023/a:1015005628871
• 作为产物：
  描述：

  tetra-isopropyl dibromomethylene bisphosphonate 、 足球烯 在 tetrabutylammonium tetrafluoroborate 作用下， 以 邻二氯苯 、 乙腈 为溶剂， 以50.2%的产率得到61,61-bis(diisopropoxyphosphoryl)methano[60]fullerene
  参考文献：
  名称：

  Electrochemical synthesis of carbonyl- and phosphoryl-containing methano[60]fullerenes

  摘要：

  在黄铜电极上，在邻二氯苯-MeCN（3:1 v/v）/0.05 M Bu4NBF4，在室温下分别得到 61-(对溴苯甲酰)甲桥[60]富勒烯或 61,61-双(二异丙氧基磷酰)甲桥[60]富勒烯，收率在 50%以上。

  DOI：

  10.1007/s11172-005-0192-9

文献信息

• ——
  作者：I. A. Nuretdinov、V. P. Gubskaya、N. I. Shishikina、G. M. Fazleeva、L. Sh. Berezhnaya、I. P. Karaseva、F. G. Sibgatullina、V. V. Zverev

  DOI：10.1023/a:1015472114103

  日期：——

  The reactions of carbanions of bis(dialkoxyphosphoryl)bromomethanes with fullerenes C-60 and C-70 afforded new bis(dialkoxyphosphoryl)methanofullerenes C-60 and C-70, respectively, whose structures were established by spectroscopic methods.