methyl 3-[[7-[7-[(3-methoxycarbonylphenyl)methyl](C60-Ih)[5,6]fulleren-1-yl](C60-Ih)[5,6]fulleren-1-yl]methyl]benzoate | 1315575-48-4

• 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: methyl 3-[[7-[7-[(3-methoxycarbonylphenyl)methyl](C60-Ih)[5,6]fulleren-1-yl](C60-Ih)[5,6]fulleren-1-yl]methyl]benzoate
• CAS: 1315575-48-4
• 化学式: C₁₃₈H₁₈O₄
• 分子量: 1739.66
• InChiKey: OTNDVLNXKXHYHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  32.3
• 重原子数：
  142
• 可旋转键数：
  9
• 环数：
  66.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-[[7-[7-[(3-methoxycarbonylphenyl)methyl](C60-Ih)[5,6]fulleren-1-yl](C60-Ih)[5,6]fulleren-1-yl]methyl]benzoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 1.5h， 以64%的产率得到
  参考文献：
  名称：

  NBS-promoted oxidation of fullerene monoradicals leading to regioselective 1,4-difunctional fullerenes

  摘要：

  NBS充分促进了从单键合的富勒烯二聚体形成富勒烯阳离子，与各种亲核试剂发生反应，从而形成非对称富勒烯1,4-双加合物。

  DOI：

  10.1039/c4cc07780f
• 作为产物：
  描述：

  methyl 3-(([60]fulleren-1(2H)-yl)methyl)benzoate 在 氧气 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 18.0h， 以90%的产率得到methyl 3-[[7-[7-[(3-methoxycarbonylphenyl)methyl](C60-Ih)[5,6]fulleren-1-yl](C60-Ih)[5,6]fulleren-1-yl]methyl]benzoate
  参考文献：
  名称：

  Cu-Catalyzed C–H Amination of Hydrofullerenes Leading to 1,4-Difunctionalized Fullerenes

  摘要：

  A novel and highly efficient Cu-catalyzed C-H amination of the monofunctionalized hydrofullerenes for the synthesis of 1,4-difunctional fullerenes has been reported. A new series of 1,4-fullerene derivatives having various monoamine addends were synthesized in good to high yields under mild reaction conditions. The controlled experiments revealed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate followed by coupling with an amine radical.

  DOI：

  10.1021/ol403573r

文献信息

• Ni-Catalyzed direct 1,4-difunctionalization of [60]fullerene with benzyl bromides
  作者：Weili Si、Xuan Zhang、Naoki Asao、Yoshinori Yamamoto、Tienan Jin

  DOI：10.1039/c5cc01534k

  日期：——

  A new Ni-catalyzed direct 1,4-difunctionalization of [60]fullerene with various benzyl bromides has been developed. The use of a DMSO additive combined with a nickel catalyst is indispensable for the formation of 1,4-dibenzyl fullerenes with a variety of functional groups. The reaction proceeds through the formation of a fullerene monoradical species.

  已经开发了一种新的Ni催化的[60]富勒烯与各种苄基溴的直接1,4-二官能化反应。DMSO添加剂与镍催化剂结合使用对于形成具有各种官能团的1,4-二苄基富勒烯是必不可少的。反应通过形成富勒烯单自由基物质而进行。
• NaOH-Catalyzed Dimerization of Monofunctionalized Hydrofullerenes: Transition-Metal-Free, General, and Efficient Synthesis of Single-Bonded [60]Fullerene Dimers
  作者：Shirong Lu、Tienan Jin、Ming Bao、Yoshinori Yamamoto

  DOI：10.1021/ol301435m

  日期：2012.7.6

  NaOH-catalyzed homo- and cross-dimerizations of monofunctionalized hydrofullerenes are reported. Various single-bonded fullerene dimers were synthesized under mild reaction conditions with remarkably high yields. The use of a NaOH catalyst combined with tetrahydrofuran as a cosolvent under an air atmosphere is critical in achieving highly efficient catalytic dimerization.

  据报道，空前的，无过渡金属的NaOH催化的单官能化氢富勒烯的均二和交叉二聚反应。在温和的反应条件下以高产率合成了各种单键富勒烯二聚体。在空气气氛下使用与四氢呋喃结合的NaOH催化剂作为助溶剂对于实现高效催化二聚至关重要。