phenyl(C60-I_h)[5,6]fullerene-1(9H)-yl ketone

• 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: phenyl(C60-I_h)[5,6]fullerene-1(9H)-yl ketone
• 英文别名: 1-benzoyl-1,2-dihydro[60]fullerene；9H-(C60-Ih)[5,6]fulleren-1-yl(phenyl)methanone
• 化学式: C₆₇H₆O
• 分子量: 826.784
• InChiKey: ZPISJCNMAWPWFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.6
• 重原子数：
  68
• 可旋转键数：
  2
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  phenyl(C60-I_h)[5,6]fullerene-1(9H)-yl ketone 在 basic Al₂O₃ 作用下， 以99%的产率得到1,2-二氢[60]富勒烯
  参考文献：
  名称：

  酰化富勒烯水解一步合成富勒烯氢化物C 60 H 2

  摘要：

  迄今未开发的一类酰化富勒烯化合物已被证明是出色的C 60 H 2前体。在用碱性Al 2 O 3进行简单处理后，它们被定量水解为C 60 H 2。这一关键特征导致开发了一种新的，直接的方案，用于选择性合成最简单的[60]富勒烯氢化物C 60 H 2。该协议可以为先前已知的C 60 H 2合成方法提供有利的替代方法，从而可以快速获得C 60 H 2。 收率高，纯度高，无需繁琐的分离过程。

  DOI：

  10.1021/jo900934j
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 以90%的产率得到phenyl(C60-I_h)[5,6]fullerene-1(9H)-yl ketone
  参考文献：
  名称：

  Ring-Opening Reaction of Cyclopropanated [60]Fullerenes:  Unexpected Transformation of Methano[60]fullerenes Having an Electron-Donating Group on the Methano-Bridge Carbon

  摘要：

  A series of novel transformations of [60] fullerene derivatives were found, starting from methano[60] fullerenes with an electron-donating group on the methano-bridge carbon. Aminomethano[60]fullerenes, in situ generated by the treatment of their trifluoromethanesulfonic acid salts with a base, were readily converted into 1-acyl-1,2-dihydro[60] fullerenes via the ring opening of the cyclopropane moiety. The aldehyde/ ketones thus obtained were easily hydrolyzed to give 1,2-dihydro[60] fullerene in the presence of hydroxide anions.

  DOI：

  10.1021/ol0705705

文献信息

• Synthesis and properties of ion-radical salts based on bis(arene)chromium complexes and fullerene derivatives
  作者：G. V. Markin、S. Yu. Ketkov、M. A. Lopatin、V. A. Kuropatov、A. S. Shavyrin、V. K. Cherkasov、G. A. Domrachev

  DOI：10.1007/s11172-014-0521-y

  日期：2014.4

  A reaction of bis(arene)chromium complexes with [60]fullerene derivatives leads to ionradical bis(arene)chromium [60]fullerides. Bis(1,2,4,5-tetramethylbenzene)chromium [70]fulleride was synthesized similarly. The compounds obtained were characterized by spectroscopic methods, their thermal decomposition was studied and thermal stability of their dimers was evaluated.

  双(芳烃)铬配合物与[60]富勒烯衍生物的反应产生离子基双(芳烃)铬[60]富勒烯化物。双(1,2,4,5-四甲基苯)铬[70]富勒烯的合成方法类似。获得的化合物通过光谱方法表征，研究了它们的热分解并评估了它们的二聚体的热稳定性。
• Tzirakis, Manolis D.; Orfanopoulos, Michael, Journal of the American Chemical Society, 2009, vol. 131, p. 4063 - 4069
  作者：Tzirakis, Manolis D.、Orfanopoulos, Michael

  DOI：——

  日期：——
• A new synthesis of fullerenyl ketones catalyzed by Ti(Oi-Pr)4
  作者：Usein M. Dzhemilev、Marina A. Famutdinova、Natal’ya R. Popod’ko、Airat R. Tuktarov

  DOI：10.1016/j.tetlet.2013.04.034

  日期：2013.6

  The reaction of fullerene C-60 with aryl carboxylates and EtMgBr in the presence of Ti(Oi-Pr)(4) as the catalyst leads to the formation of novel fullerenyl ketones. (C) 2013 Elsevier Ltd. All rights reserved.
• One-step Synthesis of Fullerene Hydride C₆₀H₂ via Hydrolysis of Acylated Fullerenes
  作者：Manolis D. Tzirakis、Mariza N. Alberti、Leanne C. Nye、Thomas Drewello、Michael Orfanopoulos

  DOI：10.1021/jo900934j

  日期：2009.8.7

  The hitherto unexplored class of acylated fullerene compounds has been shown to be excellent C60H2 precursors. Upon a simple treatment with basic Al2O3, they are hydrolyzed quantitatively into C60H2. This key feature led to the development of a new, straightforward protocol for the selective synthesis of the simplest [60]fullerene hydride, C60H2. This protocol may offer an advantageous alternative

  迄今未开发的一类酰化富勒烯化合物已被证明是出色的C 60 H 2前体。在用碱性Al 2 O 3进行简单处理后，它们被定量水解为C 60 H 2。这一关键特征导致开发了一种新的，直接的方案，用于选择性合成最简单的[60]富勒烯氢化物C 60 H 2。该协议可以为先前已知的C 60 H 2合成方法提供有利的替代方法，从而可以快速获得C 60 H 2。 收率高，纯度高，无需繁琐的分离过程。
• Ring-Opening Reaction of Cyclopropanated [60]Fullerenes:  Unexpected Transformation of Methano[60]fullerenes Having an Electron-Donating Group on the Methano-Bridge Carbon
  作者：Tomoyuki Tada、Yasuhiro Ishida、Kazuhiko Saigo

  DOI：10.1021/ol0705705

  日期：2007.5.1

  A series of novel transformations of [60] fullerene derivatives were found, starting from methano[60] fullerenes with an electron-donating group on the methano-bridge carbon. Aminomethano[60]fullerenes, in situ generated by the treatment of their trifluoromethanesulfonic acid salts with a base, were readily converted into 1-acyl-1,2-dihydro[60] fullerenes via the ring opening of the cyclopropane moiety. The aldehyde/ ketones thus obtained were easily hydrolyzed to give 1,2-dihydro[60] fullerene in the presence of hydroxide anions.