1',5'-dihydro-1'-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-2'H-[5,6]fullero-C60-I_h-[1,9-c]pyrrole | 202583-39-9

• 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',5'-dihydro-1'-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-2'H-[5,6]fullero-C60-I_h-[1,9-c]pyrrole
• 英文别名: N-(3,6,9-trioxadecyl)-3,4-fulleropyrrolidine
• CAS: 202583-39-9
• 化学式: C₆₉H₁₉NO₃
• 分子量: 909.915
• InChiKey: UCCLGPFVIZZVRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  73
• 可旋转键数：
  9
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1',5'-dihydro-1'-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-2'H-[5,6]fullero-C60-I_h-[1,9-c]pyrrole 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以37.3%的产率得到
  参考文献：
  名称：

  [60]Fullerene−Pyrrolidine-N-oxides

  摘要：

  Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The H-1 NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a N-15 isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.

  DOI：

  10.1021/jo052388s
• 作为产物：
  描述：

  聚合甲醛 、 足球烯 、 N-(3,6,9-Trioxadecyl)glycine 生成 1',5'-dihydro-1'-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-2'H-[5,6]fullero-C60-I_h-[1,9-c]pyrrole
  参考文献：
  名称：

  Antimycobacterial activity of ionic fullerene derivatives

  摘要：

  Positively charged fullerene derivatives, moderately soluble in water:DMSO 9:1, have been tested using three strains of Mycobacterium spp. Some compounds inhibit the growth of Mycobacterium tubercolosis, a human clinical isolate, particularly virulent and resistant, at doses as low as 5 mu g/mL. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00159-1

文献信息

• Antimycobacterial activity of ionic fullerene derivatives
  作者：Susanna Bosi、Tatiana Da Ros、Sabrina Castellano、Elena Banfi、Maurizio Prato

  DOI：10.1016/s0960-894x(00)00159-1

  日期：2000.5

  Positively charged fullerene derivatives, moderately soluble in water:DMSO 9:1, have been tested using three strains of Mycobacterium spp. Some compounds inhibit the growth of Mycobacterium tubercolosis, a human clinical isolate, particularly virulent and resistant, at doses as low as 5 mu g/mL. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Isolation and Characterization of All Eight Bisadducts of Fulleropyrrolidine Derivatives
  作者：Konstantinos Kordatos、Susanna Bosi、Tatiana Da Ros、Alfonso Zambon、Vittorio Lucchini、Maurizio Prato

  DOI：10.1021/jo001708z

  日期：2001.4.1

  We report the isolation and characterization of bisadducts of fulleropyrrolidine derivatives. The compounds were characterized by means of a variety of spectroscopic techniques, including ES-MS, UV-vis, H-1 NMR, and C-13 NMR. The whole series of bisadducts was separated for the first time in the case of the bispyrrolidines, and the determination of their structure was obtained by NMR spectroscopy with the help of HMQC and HMBC techniques.
• [60]Fullerene−Pyrrolidine-<i>N</i>-oxides
  作者：Peter Brough、Cedric Klumpp、Alberto Bianco、Stephane Campidelli、Maurizio Prato

  DOI：10.1021/jo052388s

  日期：2006.3.1

  Eight members of a new family of fullerene derivatives, [60]fulleropyrrolidine-N-oxides, have been synthesized and characterized. Facile oxidation, by a peracid, of the parent [60]fulleropyrrolidine gave clean conversions into the product molecules, in which the tertiary amine is transformed into a quaternary amine bearing an oxygen atom. The reaction is very selective, favoring the nitrogen atom of the pyrrolidine ring in preference to epoxidation of the fullerene cage. The H-1 NMR shows an AB quartet splitting pattern, characteristic of nonequivalent hydrogens in the pyrrolidine ring and at a chemical shift displacement of 0.8 ppm downfield. Other methods of characterization are described, including MS, differential scanning calorimetry, thermogravimetric analysis, HPLC, UV/vis, and IR. Conclusive evidence for the formation of an N-oxide moiety is provided by the synthesis, oxidation, and NMR characterization of a novel [60]fulleropyrrolidine containing a N-15 isotope, showing an 85 ppm downfield heteroatom chemical shift. Preliminary details of the effects of substitution on the reactivity of the pyrrolidine ring are also reported.