| 1332704-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 1332704-96-7
• 化学式: C₇₄H₁₄O₂
• 分子量: 934.924
• InChiKey: OANXRDHSHIAVQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.59
• 重原子数：
  76.0
• 可旋转键数：
  6.0
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,9-(4-hydroxycyclohexano)buckminsterfullerene 、 丙炔酸 在 对甲苯磺酸 、 1-氯萘 作用下， 以 甲苯 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Improved synthesis of fullerynes by Fisher esterification for modular and efficient construction of fullerene polymers with high fullerene functionality

  摘要：

  For the first time, the scope of Fisher esterification has been extended to fullerene derivatives to improve the synthesis of alkyne-functionalized fullerenes (fullerynes) using 1-chloronaphthalene as a solvent and a specially-designed, home-made reactor to promote high yield. The design allows for higher solubility of fullerene derivatives and a continuous azeotropic distillation for the removal of water to drive the reaction to completion with yields >90%. Both fullerynes (Fulleryne01 and Fulleryne02) were found to "click" to polymers, such as azide-functionalized poly(epsilon-caprolactone) (PCL-N(3)), in high efficiency without the need for fractionation. As evidenced by (1)H NMR, (13)C NMR, size exclusion chromatography, and matrix assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry, the fullerene polymers thus obtained possess well-defined structure, narrow polydispersity (similar to 1.01 by MALDI-TOF mass spectrometry; similar to 1.03 by size exclusion chromatography), and high fullerene functionality (similar to 100%). They can serve as model compounds for the investigations of polymer structures and dynamics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.07.026

文献信息

• [EN] PROCESS AND METHOD FOR THE EFFICIENT PREPARATION OF FULLERYNES<br/>[FR] PROCÉDÉ ET MÉTHODE POUR LA PRÉPARATION EFFICACE DE FULLERYNES
  申请人：UNIV AKRON

  公开号：WO2012005762A1

  公开（公告）日：2012-01-12

  The preparation of novel fullerynes which are fullerenes (e.g. C60, C70, C80, etc.) that contain one or more alkyne functionalities and may contain additional functional groups such as hydroxyls, halogens, esters, haloesters, phenyl, oligo(ethylene glycol)s, perfluorinated alkyl chains, and the like. Two desired preparation routes are disclosed. The first one is the Fischer esterification in desired solvents using a special designed reactor in contrast to the heretofore initial Steglich reaction that results in side reactions and low yields. The second one uses acetylide Grignard reagents that have reduced nucleophilicity and higher stability in contrast to the use of heretofore initial lithium organyls or other Grignard reagents that would add to C60 with possible multi-additions in an uncontrollable manner.

  制备新型富勒烯，该富勒烯（例如C60，C70，C80等）含有一个或多个炔基官能团，并可能含有额外的官能团，例如羟基，卤素，酯，卤代酯，苯基，寡聚（乙二醇）和全氟烷基等。文中介绍了两种所需的制备路线。第一种是在特定溶剂中使用特殊设计的反应器进行Fischer酯化反应，与此前的Steglich反应相比，可以避免副反应和低收率。第二种方法使用乙炔基格氏试剂，其亲核性降低且稳定性更高，相比于此前使用的锂有机化合物或其他格氏试剂，可以避免多次无法控制的加成反应。