methyl 3-(([60]fulleren-1(2H)-yl)methyl)benzoate | 1315575-66-6

• 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-(([60]fulleren-1(2H)-yl)methyl)benzoate
• 英文别名: methyl 3-[([60]fulleren-1(2H)-yl)methyl]benzoate；methyl 3-(9H-(C60-Ih)[5,6]fulleren-1-ylmethyl)benzoate
• CAS: 1315575-66-6
• 化学式: C₆₉H₁₀O₂
• 分子量: 870.837
• InChiKey: QVGKXCWBSMZVNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.3
• 重原子数：
  71
• 可旋转键数：
  4
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  足球烯 、 3-(溴甲基)苯甲酸甲酯 在 锰 、 [1,2-双(二苯基膦)乙烷]二氯钴(II) 、 水 作用下， 以 邻二氯苯 为溶剂， 反应 48.0h， 以58%的产率得到methyl 3-(([60]fulleren-1(2H)-yl)methyl)benzoate
  参考文献：
  名称：

  [60]富勒烯与活性烷基溴的钴催化加氢烷基化：单烷基化富勒烯的选择性合成

  摘要：

  C(60) 与反应性烷基溴化物 1 (RBr) 在 Mn 还原剂和 H(2)O 在环境温度下的共催化加氢烷基化得到单烷基化的 C(60) (2) 以良好到高产率。在 Ar 气氛下使用 CoLn/Mn/H(2)O 是目前转型成功的关键。该反应最有可能通过 Co(0 或 I) 配合物促进生成自由基 (R(•))，然后添加到 C(60)。这种加氢烷基化方法适用于合成附有 C(60) (2l) 的锌卟啉、附有 C(60) (2m) 的树枝状聚合物和富勒烯二聚体 (2n)，这些化合物不容易通过先前已知的方法获得。

  DOI：

  10.1021/ja204982w

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。
• Highly Efficient Cu(OAc)2-Catalyzed Dimerization of Monofunctionalized Hydrofullerenes Leading to Single-Bonded [60]Fullerene Dimers
  作者：Shirong Lu、Tienan Jin、Eunsang Kwon、Ming Bao、Yoshinori Yamamoto

  DOI：10.1002/anie.201107505

  日期：2012.1.16

  Dimers are a girl's best friend: The title reaction allows the formation of single‐bonded fullerene dimers with extremely high chemical yield and high compatibility with various functional groups, which are highly soluble in organic solvents. The use of Cu(OAc)2 catalyst with dimethylformamide or acetonitrile as additives under air is the critical factor in achieving the highly efficient catalytic

  二聚体是女孩最好的朋友：标题反应可形成单键富勒烯二聚体，其化学收率极高，并且与高度溶于有机溶剂的各种官能团具有高度相容性。在空气中使用带有二甲基甲酰胺或乙腈作为添加剂的Cu（OAc）2催化剂是实现高效催化二聚的关键因素。
• Functional 2-benzyl-1,2-dihydro[60]fullerenes as acceptors for organic photovoltaics: facile synthesis and high photovoltaic performances
  作者：Shirong Lu、Tienan Jin、Takeshi Yasuda、Ashraful Islam、Md. Akhtaruzzaman、Liyuan Han、Khalid A. Alamry、Samia A. Kosa、Abdullah Mohamed Asiri、Yoshinori Yamamoto

  DOI：10.1016/j.tet.2012.11.099

  日期：2013.1

  A new series of functional 2-benzyl-1,2-dihydro[60]fullerenes, BnHCs, were synthesized efficiently via co-catalyzed selective monofunctionalization of C-60 with functional benzyl bromides. Photophysical and electrochemical properties of the new BnHCs were investigated. PSCs based on 2-MeO-4-CO2Me-BnHC as new acceptor and P3HT as donor showed a power conversion efficiency of 3.75%, which is comparable to that of PC61BM under the same device conditions. (c) 2012 Elsevier Ltd. All rights reserved.