1,2-(3',5'-cyclohexadieno)buckminsterfullerene | 827043-81-2

• 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: 1,2-(3',5'-cyclohexadieno)buckminsterfullerene
• CAS: 827043-81-2
• 化学式: C₆₄H₄
• 分子量: 772.736
• InChiKey: ZHTDPGBITWFENH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.42
• 重原子数：
  64.0
• 可旋转键数：
  0.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1,2-(3',5'-cyclohexadieno)buckminsterfullerene 在 氧气 作用下， 以 二硫化碳 、 氘代氯仿 为溶剂， 反应 12.0h， 生成 1,2-(3',5'-cyclohexadieno)buckminsterfullerene 3',6'-endoperoxide
  参考文献：
  名称：

  A Methodology for the Reversible Solubilization of Fullerenes

  摘要：

  The poor solubility of certain fullerene derivatives, especially those bearing several fullerene moieties, has hampered the preparation of new materials. We are proposing a strategy which uses fullerenes bearing a readily removable solubilizing group to carry out reaction steps leading to a final product with intrinsic low solubility. This is now possible with the one-step conversion of the t-BOC derivative 8a to C-60 in over 95% yield. This one-pot conversion involves the in situ formation of diene 4 which, after [4 + 2] cycloaddition with dimethyl acetylenedicarboxylate, affords the bicyclic adduct 11 undergoing rapid cycloreversion to C-60 and dimethyl phthalate. This method was tested with two functionalized C-60 derivatives (14 and 18) as a first step toward the preparation of new nanosized molecular allotropes of carbon and rigid fullerene-rich polymers.

  DOI：

  10.1021/jo00125a022
• 作为产物：
  描述：

  1,2-(5'-hydroxy-3'-cyclohexeno)buckminsterfullerene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以48%的产率得到1,2-(3',5'-cyclohexadieno)buckminsterfullerene
  参考文献：
  名称：

  A Methodology for the Reversible Solubilization of Fullerenes

  摘要：

  The poor solubility of certain fullerene derivatives, especially those bearing several fullerene moieties, has hampered the preparation of new materials. We are proposing a strategy which uses fullerenes bearing a readily removable solubilizing group to carry out reaction steps leading to a final product with intrinsic low solubility. This is now possible with the one-step conversion of the t-BOC derivative 8a to C-60 in over 95% yield. This one-pot conversion involves the in situ formation of diene 4 which, after [4 + 2] cycloaddition with dimethyl acetylenedicarboxylate, affords the bicyclic adduct 11 undergoing rapid cycloreversion to C-60 and dimethyl phthalate. This method was tested with two functionalized C-60 derivatives (14 and 18) as a first step toward the preparation of new nanosized molecular allotropes of carbon and rigid fullerene-rich polymers.

  DOI：

  10.1021/jo00125a022