| 151569-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 151569-29-8
• 化学式: C₇₄H₁₀
• 分子量: 898.893
• InChiKey: WZWOBZCVVJXWED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  74
• 可旋转键数：
  0
• 环数：
  37.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  反应 0.17h， 生成 足球烯 、 9',9",10',10"-tetrahydrobis[9,10]ethanoanthra[11',12':1,9;11",12":52,60][5,6]fullerene-C60-I_h
  参考文献：
  名称：

  Kraeutler, Bernhard; Mueller, Thomas; Maynollo, Joseph, Angewandte Chemie, 1996, vol. 108, # 11, p. 1294 - 1296

  摘要：

  DOI：
• 作为产物：
  描述：

  蒽 、 足球烯 在 水 、 2C₅₅H₃₄BN₉O*3C₆H₁₆N₂Pd⁽²⁺⁾*6NO₃^(1-) 作用下， 以 二甲基亚砜 为溶剂， 以6%的产率得到
  参考文献：
  名称：

  9-官能化蒽与 C60/C70 在水溶性亚酞菁笼腔内的 Diels-Alder 反应的加速

  摘要：

  介绍 分子笼状容器可以通过创建合适的亲水/疏水环境来在其空腔中容纳各种客体分子，在该环境中发生稳定的相互作用。1分子胶囊的中心空腔让人想起酶活性位点，因此，它们被用作进行化学反应的催化袋。2有限空间内底物的邻近性和明确的组织大大降低了反应的熵成本，从而导致反应速率显着提高。3在这种背景下，超分子配位笼作为人工催化剂引起了相当大的关注，因为它们具有结构坚固的优点，并且通过金属离子和有机配体的模块化方法易于制备。4 在自组装配位纳米笼的空腔中进行了不同类型的转化。2, 5特别相关的是在生态友好的水介质中进行的那些，使用水溶性分子主体，为不溶性疏水底物的封装创造疏水环境。6最近，我们报道了使用水溶性金属有机亚酞菁 (SubPc) 笼（图 1 中的SubPc-cage ）在水介质中进行富勒烯功能化的典型示例。7 SubPcs 是碗形芳香族发色团，由于具有良好的形状互补性，与 C 60和 C 70的球形

  DOI：

  10.1002/adsc.202301336

文献信息

• Regioselective `One-Pot' Synthesis of Antipodal Bis-adducts by Heating of Solid [5,6]Fullerene-C60-Ih and Anthracenes, Preliminary Communication
  作者：Alvaro Duarte-Ruiz、Klaus Wurst、Bernhard Kräutler

  DOI：10.1002/1522-2675(20010815)84:8<2167::aid-hlca2167>3.0.co;2-v

  日期：2001.8.15

  6]fullerene-C60-Ih (1) with some anthracenes were prepared highly regioselectively by heating mixtures of the solid 1 and anthracene or of (one of) three alkyl-substituted anthracenes in the absence of solvents (Scheme 2). Other bis-cycloadducts were not detected, but lesser amounts of mono-cycloadducts 2 and 4 – 6, respectively, were also formed. Heating of solvent-free mixtures of 1 and three other alkyl-substituted

  通过加热固体 1 和蒽的混合物或在没有溶剂的情况下，三个烷基取代的蒽中的一个（方案 2）。未检测到其他双环加合物，但也分别形成了较少量的单环加合物 2 和 4-6。加热 1 种和三种其他烷基取代的蒽的无溶剂混合物不会产生可检测量的（对映体）双环加合物。通过 X 射线晶体学分析了 1 和 1-甲基蒽的对映双加合物 7。加热蒽和固体 1 的制备结果与加热蒽和 1 的相应结晶单加合物的结果平行。这两种方法都揭示了反应对蒽单元上烷基取代基的存在和位置的显着一致依赖性。来自蒽和 1 的对映双加合物的区域选择性组装不能通过它们（固有的分子）稳定性来合理化，但它表明晶格的关键控制。
• Nematic self-organization of regioselectively polyfunctionalized [60]fullerene
  作者：Hind Mamlouk-Chaouachi、Benoît Heinrich、Cyril Bourgogne、Daniel Guillon、Bertrand Donnio、Delphine Felder-Flesch

  DOI：10.1039/c1jm10982k

  日期：——

  The attempt to elaborate organic materials at the nanoscale has attracted broad attention in the last few years. Here, we report the synthesis and characterization of new polypedic organic materials possessing the [60]fullerene as the three-dimensional rigid scaffold. High molecular weight hexakisadducts with different symmetries were obtained in 40 to 60% yield through modulations of the A. Hirsch's and B. Kraütler's methodologies. Such a regioselective grafting of side-connected malonates on C60 put in evidence that not only the size but also the nature of the malonate influences very strongly the optimal reaction conditions to the preparation of multiadducts with very good yields. Characterization was complemented by an investigation of their thermotropic behaviour. Starting from non-mesogenic precursors, the 3D organization stemming from the regioselective polyfunctionalization of the carbon nanosphere allowed highlighting an original nematic self-organization (no literature equivalent) which could be partially oriented under a magnetic field at room temperature.

  过去几年中，在纳米尺度上精心制作有机材料的尝试引起了广泛关注。在此，我们报告了以 [60] 富勒烯为三维刚性支架的新型多肽有机材料的合成和表征。通过修改 A. Hirsch 和 B. Kraütler 的方法，我们获得了具有不同对称性的高分子量六烷基加合物，产率为 40% 至 60%。在 C60 上进行侧连接丙二酸盐的这种区域选择性接枝证明，丙二酸盐的大小和性质对制备多加成物的最佳反应条件有很大影响，而且产率非常高。除了表征之外，还对它们的趋热行为进行了研究。从非介电前体开始，碳纳米圈的区域选择性多官能化产生的三维组织使其突出了一种原始的向列自组织（无文献对应），在室温磁场下可部分定向。
• Supramolecular Subphthalocyanine Cage as Catalytic Container for the Functionalization of Fullerenes in Water
  作者：Ainhoa Salazar、Marta Moreno‐Simoni、Sunit Kumar、Jorge Labella、Tomás Torres、Gema de la Torre

  DOI：10.1002/anie.202311255

  日期：2023.10.26

  has been shown to catalyze the Diels–Alder reaction between C60 and anthracene in water to yield mono- and bis-adducts with high regioselectivity. Catalytic amounts of the cage led to better conversions because it favours co-encapsulation of the substrates in the hydrophobic cavity. Moreover, the larger binding affinity of the cage for C60 compared to the resulting adducts enables catalytic turnover.

  金属有机 Pd(II)-亚酞菁笼已被证明可以催化 C 60和蒽在水中的 Diels-Alder 反应，生成具有高区域选择性的单加合物和双加合物。笼的催化量导致更好的转化，因为它有利于疏水空腔中基质的共封装。此外，与所得加合物相比，笼对C 60的更大结合亲和力能够实现催化转换。
• Kinetics of the Diels–Alder reaction between C60 and acenes
  作者：Ginka H. Sarova、Mário N. Berberan-Santos

  DOI：10.1016/j.cplett.2004.09.005

  日期：2004.10

  The kinetics of the Diels-Alder reactions between C-60 and the linear acenes anthracene and tetracene are studied in toluene, in the temperature range 22-63 degreesC. It is observed that tetracene reacts much more readily with C-60 than does anthracene. The different reactivities of anthracene and tetracene towards C-60 correlate with the respective aromaticity loss upon cycloaddition, as previously predicted theoretically. The two monoadducts also display different kinetics as regards the dissociation back to the reagents. In the studied temperature range, tetracene monoadduct decomposition by retro-Diels Alder reaction is negligible, while the anthracene monoadduct is unstable above room temperature. (C) 2004 Elsevier B.V. All rights reserved.
• Cycloadditions to [60]fullerene using microwave irradiation: A convenient and expeditious procedure
  作者：Pilar de la Cruz、Antonio de la Hoz、Fernando Langa、Beatriz Illescas、Nazario Martin

  DOI：10.1016/s0040-4020(96)01150-7

  日期：1997.2

  Several Diels-Alder and 1,3-dipolar cycloadditions to C-60 were performed, under microwave irradiation, in a modified domestic microwave oven and a focused microwave reactor. Reactions proceed within minutes to afford the respective cycloadducts in similar or increased yields related to the described methods by conventional heating. This methodology simplifies the procedure and overcomes the drawbacks resulting from the long reaction times required under classical heating conditions. (C) 1997, Elsevier Science Ltd.