methyl 3-methoxy-4-(([60]fulleren-1(2H)-yl)methyl)benzoate | 1418003-38-9

• 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-methoxy-4-(([60]fulleren-1(2H)-yl)methyl)benzoate
• CAS: 1418003-38-9
• 化学式: C₇₀H₁₂O₃
• 分子量: 900.863
• InChiKey: DLXBXSZVROCPHR-IIPMEGKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.18
• 重原子数：
  73.0
• 可旋转键数：
  4.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  吗啉 、 methyl 3-methoxy-4-(([60]fulleren-1(2H)-yl)methyl)benzoate 在 氧气 、 copper(ll) bromide 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 13.0h， 以71%的产率得到1-(morpholino)-4-[4-(methoxycarbonyl)-2-methoxylbenzyl]-1,4-dihydro[60]fullerene
  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：

  4-溴甲基-3-甲氧基苯甲酸甲酯 、 足球烯 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60%的产率得到methyl 3-methoxy-4-(([60]fulleren-1(2H)-yl)methyl)benzoate
  参考文献：
  名称：

  Functional 2-benzyl-1,2-dihydro[60]fullerenes as acceptors for organic photovoltaics: facile synthesis and high photovoltaic performances

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.11.099

文献信息

• NHC-Catalyzed Three-Component Hydroalkylation Reactions of [60]Fullerene: An Umpolung Approach to Diverse Monoalkylated Hydrofullerenes
  作者：Tong-Xin Liu、Xue Zhu、Shilu Xia、Xin Wang、Pengling Zhang、Guisheng Zhang

  DOI：10.1021/acs.orglett.2c01301

  日期：2022.5.27

  A novel N-heterocyclic carbene-catalyzed three-component umpolung hydroalkylation of [60]fullerene with 4-(chloromethyl)-benzaldehydes/α,β-unsaturated aldehydes and alcohols/thioalcohols has been developed for the flexible and efficient preparation of diverse monoalkylated hydrofullerenes. Organic catalysis, broad substrate scope, excellent functional group tolerance, and products with high diversity

  开发了一种新型N-杂环卡宾催化的 [60] 富勒烯与 4-(氯甲基)-苯甲醛/α,β-不饱和醛和醇/硫醇的三组分 umpolung 加氢烷基化反应，用于灵活有效地制备各种单烷基化加氢富勒烯. 有机催化、广泛的底物范围、出色的官能团耐受性以及具有高度多样性和复杂性的产品是该协议的吸引人的特点。