| 177726-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• CAS: 177726-22-6
• 化学式: C₆₆H₁₄N₂
• 分子量: 834.851
• InChiKey: INOQMFSHBVINCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  68
• 可旋转键数：
  0
• 环数：
  34.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  、 碘甲烷 生成 C60-bis(N,N-dimethylpyrrolidinium iodide)
  参考文献：
  名称：

  Anti-HIV properties of cationic fullerene derivatives

  摘要：

  A series of regioisomeric bis-fulleropyrrolidines bearing two ammonium groups have been synthesized and their activities against HIV-1 and HIV-2 have been evaluated. Two trans isomers have been endowed with interesting antiviral properties, confirming the importance of the relative positions of the substituent on the C-60 cage. In addition, reduced amphiphilicity of molecules to other compounds previously reported decreases their cytotoxicity in CEM cell cultures. None of the compounds showed any inhibitory activity against a variety of DNA and RNA viruses other than HIV. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.069
• 作为产物：
  描述：

  聚合甲醛 、 肌氨酸 、 N-Methylfulleropyrrolidine 以 甲苯 为溶剂， 反应 4.0h， 以6.8%的产率得到
  参考文献：
  名称：

  使用激发三重态的瞬态 EPR 光谱进行富勒烯 C60 双加合物的结构分配

  摘要：

  瞬态 EPR 光谱已被用于测量两个系列富勒烯双加合物中激发三重态的光谱。已分析了 C60 与双（乙氧基羰基）亚甲基和五种双-N-甲基吡咯烷的八种不同双加合物。电子偶极相互作用的 D 和 E 参数以及说明自旋极化的零场三线态子能级的数量已通过光谱模拟确定。对于每个双加合物，它们看起来都很奇特。结果表明，三重 EPR 技术代表了一种有用的光谱工具，可以对 C60 的双加合物进行结构分配。

  DOI：

  10.1021/ja9709583

文献信息

• Preparation and Characterization of Six Bis(<i>N</i>-methylpyrrolidine)−C₆₀ Isomers:  Magnetic Deshielding in Isomeric Bisadducts of C₆₀
  作者：Qing Lu、David I. Schuster、Stephen R. Wilson

  DOI：10.1021/jo960466t

  日期：1996.1.1

  A series of isomers of bis(N-methylpyrrolidine)-C(60) 2 (Prato bisadducts) was prepared by the 1,3-dipolar cycloaddition of N-methylazomethine ylide to C(60). Six isomers were separated and characterized by ESI-MS, UV/vis, and (1)H and (13)C NMR spectroscopy. The structures of these bisadducts were assigned based on (1) comparison of their molecular symmetries with their (1)H and (13)C NMR spectra

  通过将N-甲基偶氮甲叉基内酯的1，3-偶极环加成到C（60）上，制备了一系列双（N-甲基吡咯烷）-C（60）2的异构体（普拉托双加合物）。分离了六个异构体，并通过ESI-MS，UV / vis和（1）H和（13）C NMR光谱进行了表征。这些双加合物的结构是根据（1）比较其分子对称性与（1）H和（13）C NMR光谱，（2）将其UV / vis光谱与相应的Bingel-Hirsch双加合物的结构， （3）亚甲基和N-甲基（1）H NMR共振的脱保护顺序。普拉托（Brato）双加成比对C（60）的Bingel-Hirsch双加成具有较低的化学选择性。
• Isolation and Characterization of Nine Tris-adducts of <i>N</i>-Methylfulleropyrrolidine Derivatives
  作者：Silvia Marchesan、Tatiana Da Ros、Maurizio Prato

  DOI：10.1021/jo050417t

  日期：2005.6.1

  We report the isolation and characterization of bis- and tris-adducts of fulleropyrrolidine derivatives. First, all eight N-methyl regioisomers with two addends on the C-60 sphere have been isolated; second, C-60 was used as starting material for the synthesis of tris-adducts, and the products formed in detectable quantities have been isolated and characterized. Third, the same compounds were obtained by introducing the third addend on each previously isolated bis-derivative: this approach facilitated the assignment of the relative geometry through chromatographic comparison of the diverse reaction mixtures. Finally, the obtained tris-adducts have been characterized by means of ES-MS, UV-vis, H-1 NMR, as well as comparison with UV spectra and elution order of Bingel and Diels-Alder tris-adducts described in the literature.
• Probing the Electron-Accepting Reactivity of Isomeric Bis(pyrrolidinium) Fullerene Salts in Aqueous Solutions
  作者：Dirk M. Guldi

  DOI：10.1021/jp9933931

  日期：2000.2.1

  Series of water-soluble isomer bis(pyrrolidinium) salts, with C-60(C4H10N+)(2) as cationic moiety (2a-2d), were probed in radical- and light-induced reduction studies and compared to bis(carboxylates) C-60[C(COO-)(2)](2) and to gamma-CD-encapsulated C-60 Pulse radiolytic reduction of 2a-2d with hydrated electrons and (CH3)(2). COH radicals leads to the formation of the fullerene pi-radical anion, exhibiting fingerprint absorption characteristics in the near-IR region. Because of the electron-withdrawing nature of the pyrrolidinium groups the electron-acceptor properties of the investigated bis(pyrrolidinium) salts are markedly improved relative to the bis(carboxylates) (C-60[C(COO-)(2)](2)) and also relative to C-60. For example, the rate constants for the fullerene reduction of 2a-2d with hydrated electrons ((0.88-2.2) x 10(10) M-1 s(-1)) and (CH3)(2). COH radicals ((4.7-7.1) x 10(8) M-1 s(-1)) are clearly faster than those noted for C-60[C(COO-)(2)](2) (e(aq)(-): (0.19-0.34) x 10(10) M-1 s(-1); (CH3)(2). COH: (0.9-2.2) x 10(8) M-1 s(-1)), and C-60 (e(aq)(-): 1.8 x 10(10) M-1 s(-1); (CH3)(2). COH: 2.7 x 10(8) M-1 s-'). Photolysis of 2a-2d gives rise to singlet excited state absorptions that closely resemble earlier observations for the pyrrolidine precursor, e.g., C-60(C3H7N)(2) (1a-1d) in deoxygenated toluene solutions. The triplet lifetimes of 2a-2d, as measured by nanosecond-resolved photolysis, are typically around 33 mu s, similar to the triplet lifetimes of truly monomeric fullerene solutions. Quenching experiments with diazabicyclooctane (DABCO), involving the tripler excited states of 2a-2d, yielded rate constants which vary between 2.5 x 10(6) and 4.7 x 10(6) M-1 s(-1) and reveal a slow-down relative to C-60 (7.4 x 10(7) M-1 s(-1)).
• Anti-HIV properties of cationic fullerene derivatives
  作者：Silvia Marchesan、Tatiana Da Ros、Giampiero Spalluto、Jan Balzarini、Maurizio Prato

  DOI：10.1016/j.bmcl.2005.05.069

  日期：2005.8

  A series of regioisomeric bis-fulleropyrrolidines bearing two ammonium groups have been synthesized and their activities against HIV-1 and HIV-2 have been evaluated. Two trans isomers have been endowed with interesting antiviral properties, confirming the importance of the relative positions of the substituent on the C-60 cage. In addition, reduced amphiphilicity of molecules to other compounds previously reported decreases their cytotoxicity in CEM cell cultures. None of the compounds showed any inhibitory activity against a variety of DNA and RNA viruses other than HIV. (c) 2005 Elsevier Ltd. All rights reserved.
• Use of Transient EPR Spectroscopy of Excited Triplet State for the Structural Assignment of Bisadducts of Fullerene C₆₀
  作者：Luigi Pasimeni、Andreas Hirsch、Iris Lamparth、Andrea Herzog、Michele Maggini、Maurizio Prato、Carlo Corvaja、Gianfranco Scorrano

  DOI：10.1021/ja9709583

  日期：1997.12.1

  Transient EPR spectroscopy has been applied to measure the spectra of excited triplet states in two series of fullerene bisadducts. Eight different bisadducts of C60 with bis(ethoxycarbonyl)methylene and five bis-N-methylpyrrolidines have been analyzed. The D and E parameters of electron dipolar interaction and the populations of the zero field triplet sublevels, accounting for spin polarization, have

  瞬态 EPR 光谱已被用于测量两个系列富勒烯双加合物中激发三重态的光谱。已分析了 C60 与双（乙氧基羰基）亚甲基和五种双-N-甲基吡咯烷的八种不同双加合物。电子偶极相互作用的 D 和 E 参数以及说明自旋极化的零场三线态子能级的数量已通过光谱模拟确定。对于每个双加合物，它们看起来都很奇特。结果表明，三重 EPR 技术代表了一种有用的光谱工具，可以对 C60 的双加合物进行结构分配。