1,9-(4-hydroxycyclohexano)buckminsterfullerene | 156372-25-7

• 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: 1,9-(4-hydroxycyclohexano)buckminsterfullerene
• 英文别名: 1,2-(4'-hydroxycyclohexano)[60]fullerene
• CAS: 156372-25-7
• 化学式: C₆₄H₈O
• 分子量: 792.767
• InChiKey: CXGPOVRYVMARDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.84
• 重原子数：
  65.0
• 可旋转键数：
  0.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-芘丁酸 、 1,9-(4-hydroxycyclohexano)buckminsterfullerene 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 以41%的产率得到
  参考文献：
  名称：

  发色团附加的C 60和C 70富勒烯：蒽和P衍生物–合成，循环伏安法和光谱

  摘要：

  已经研究了含有间隔连接的苯基（BK1），9-蒽基（BK2），4-（9-蒽基）苯基（BK3）和1-吡啶基（BE1和FE1）的C 60和C 70加合物。基于富勒烯与2-三甲基甲硅烷氧基-1,3-丁二烯（TB）的[4 + 2]环加成反应，采用了两种不同的合成途径。给出了新化合物的光谱数据。通过循环伏安法和光谱电化学方法进行了电化学和光电化学研究。BK2，BK3，BE1和FE1的荧光发射光谱被报道。从激发的荧光团到富勒烯亚基的分子内能量转移发生。

  DOI：

  10.1002/(sici)1099-0690(199808)1998:8<1549::aid-ejoc1549>3.0.co;2-#
• 作为产物：
  描述：

  1,2-(4'-oxacyclohexano)[60]fullerene 在 sodium tetrahydroborate 作用下， 生成 1,9-(4-hydroxycyclohexano)buckminsterfullerene
  参考文献：
  名称：

  Anti-human immunodeficiency virus activity and cytotoxicity of derivatized buckminsterfullerenes

  摘要：

  Eleven new functional derivatives of C-60 have been tested for anti-HIV activity in peripheral blood mononuclear cells infected with HIV-1(LAV). Nine compounds displayed activity in the low micromolar range (EC(50)), three of them lower than any fullerene derivative reported to date. With one exception, these compounds displayed no cytotoxicity up to 100 mu M. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00210-7

文献信息

• Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivative·gamma-cyclodextrin complexes
  作者：Atsushi Ikeda、Akiko Hirata、Michiko Ishikawa、Jun-ichi Kikuchi、Shunsuke Mieda、Wataru Shinoda

  DOI：10.1039/c3ob41513a

  日期：——

  We have demonstrated that C60 derivatives bearing a pyrrolidine moiety as well as a variety of other substituents can form 1 : 2 complexes with γ-cyclodextrin (γ-CDx) using a mechanochemical high-speed vibration milling apparatus. When the influence of the steric hindrance of the substituents on the formation of the complexes was negligible, the water-solubilities of the complexes were shown experimentally to be completely dependent on the hydrophobic properties of the substituent. Furthermore, the stabilities of the γ-CDx-complexes of several different C60 derivatives were found to be similar to or slightly higher than that of the C60·γ-CDx complex, with the solubilities of the complexes showing no correlation to the stabilities. Based on the results of a series of theoretical investigations, we have shown that the stabilities of the γ-CDx-complexes can be affected not only by steric effects but also by the polarities of the substituent groups, which exist in the vicinity of the upper rim of γ-CDx, because the water bound to the polar group can assist in the stabilisation of the complexes.

  我们利用机械化学高速振动研磨装置证明，含有吡咯烷分子以及其他多种取代基的 C60 衍生物可以与δ³-环糊精（δ³-CDx）形成 1:◎2 复合物。当取代基的立体阻碍对络合物形成的影响可以忽略不计时，实验证明络合物的水溶性完全取决于取代基的疏水性。此外，研究还发现几种不同 C60 衍生物的 δ³-CDx 复合物的稳定性与 C60Â-δ³-CDx 复合物的稳定性相似或略高于后者，而复合物的溶解度与稳定性没有相关性。根据一系列理论研究的结果，我们发现 δ³-CDx 复合物的稳定性不仅会受到立体效应的影响，还会受到存在于 δ³-CDx 上缘附近的取代基团极性的影响，因为与极性基团结合的水可以帮助稳定复合物。
• [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。
• Control of self-aggregation of fullerenes by connection with calix[4]arene: solvent- and guest-effects to particle size
  作者：Atsushi Ikeda、Taishin Irisa、Tomoe Hamano、Toyokazu Kitahashi、Yoshihiro Sasaki、Mineo Hashizume、Jun-ichi Kikuchi、Toshifumi Konishi、Seiji Shinkai

  DOI：10.1039/b513123e

  日期：——

  A new molecular design of fullerene derivatives exhibiting trigger-responsive self-aggregation in organic solvents has been established. Calix[4]arene was covalently connected with fullerene in order to apply host–guest interaction to the aggregation control. The self-assembly behaviour was studied in organic solvents by UV–vis absorption spectroscopy, dynamic light scattering and transmission electron microscopy. Results show that the bisfullerene formed self-aggregations with a low polydispersity index due to the fullerenes' tendency to aggregate in polar organic solvents. Furthermore, the aggregate sizes can be changed readily by solvent composition and the addition of guest cations. Especially, disaggregation of the bisfullerene was induced by addition of LiClO4 or NaClO4.

  一种新的富勒烯衍生物分子设计在有机溶剂中表现出触发响应的自聚集。Calix[4]arene与富勒烯共价连接，以便将主客体相互作用应用于聚集控制。通过紫外-可见吸收光谱、动态光散射和透射电子显微镜研究了有机溶剂中的自组装行为。结果表明，由于富勒烯在极性有机溶剂中聚集的趋势，双富勒烯形成了低多分散指数的自聚集。此外，聚集物的尺寸可以通过溶剂成分和添加客体阳离子来改变。特别是，双富勒烯的解聚是由添加LiClO4或NaClO4引起的。
• Target-selective photo-degradation of HIV-1 protease by a fullerene-sugar hybrid
  作者：Shuho Tanimoto、Satoshi Sakai、Shuichi Matsumura、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/b811726h

  日期：——

  A designed fullerene-sugar hybrid effectively and selectively degraded the target protein, HIV-1 protease, which has high affinity for the fullerene moiety; degradation was achieved using long-wavelength UV or visible photo-irradiation, in the absence of any additives and under neutral conditions.

  一种经过设计的富勒烯-糖混合物能够有效、选择性地降解目标蛋白——HIV-1蛋白酶，该蛋白对富勒烯部分具有高亲和力；降解过程是在没有任何添加剂且中性条件下，通过长波紫外线或可见光照射实现的。
• Toward Controlled Spacing in One-Dimensional Molecular Chains:  Alkyl-Chain-Functionalized Fullerenes in Carbon Nanotubes
  作者：Thomas W. Chamberlain、Andrew Camenisch、Neil R. Champness、G. Andrew D. Briggs、Simon C. Benjamin、Arzhang Ardavan、Andrei N. Khlobystov

  DOI：10.1021/ja071803q

  日期：2007.7.1

  A range of fullerenes (C-60) functionalized with long alkyl chains have been synthesized and inserted into single-walled carbon nanotubes. The impact of the alkyl chain length and of the type of linker between the addend and the fullerene cage on the geometry of molecular arrays in nanotube has been studied by high-resolution transmission electron microscopy. In the presence of functional groups the mean interfullerene separations are significantly increased by 2-8 nm depending on the length of the alkyl chain, but the periodicity of the fullerene arrays is disrupted due to the conformational flexibility of the alkyl groups.