N-ethyl pyrrolidino(3,4:1,2)(60)fullerene | 922176-10-1

• 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: N-ethyl pyrrolidino(3,4:1,2)(60)fullerene
• CAS: 922176-10-1
• 化学式: C₆₄H₉N
• 分子量: 791.782
• InChiKey: JBPVTKZHZROKTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.63
• 重原子数：
  65.0
• 可旋转键数：
  1.0
• 环数：
  33.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-ethyl pyrrolidino(3,4:1,2)(60)fullerene 以 邻二氯苯 为溶剂， 以73%的产率得到足球烯
  参考文献：
  名称：

  吡咯烷基富勒烯的选择性电化学逆环加成反应。

  摘要：

  DOI：

  10.1002/anie.200602431
• 作为产物：
  描述：

  N-乙甘胺酸 、 足球烯 以 邻二氯苯 为溶剂， 反应 2.5h， 以33%的产率得到N-ethyl pyrrolidino(3,4:1,2)(60)fullerene
  参考文献：
  名称：

  [60]富勒烯与氨基酸和氨基酸酯的热反应研究†

  摘要：

  研究了[60]富勒烯与一系列氨基酸和氨基酸酯在好氧和黑暗条件下的热反应。尽管没有有意地添加醛，但是从这些反应可以获得全吡咯烷。已经提出了可能的涉及罕见的C–N键断裂的反应机理，以生成醛，然后与氨基酸和氨基酸酯反应生成甲亚胺基团，然后将1,3-偶极环加成生成[60]富勒烯，从而得到全吡咯烷。对照实验支持我们提出的机制，并阐明了氨基酸和氨基酸酯的C–N键裂解的先天性。

  DOI：

  10.1039/c2ob26066b

文献信息

• Solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes under high-speed vibration milling
  作者：Guan-Wu Wang、Ting-Hu Zhang、Er-Hong Hao、Li-Juan Jiao、Yasujiro Murata、Koichi Komatsu

  DOI：10.1016/s0040-4020(02)01478-3

  日期：2003.1

  The solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes (RCHO) 2a-e under high-speed vibration milling (HSVM) conditions have been investigated. Fulleropyrrolidines 4a-e (C-60(CH2N(CH3)CHR), R=H (4a), C6H5 (4b), pNO(2)-C6H5 (4c), p-CH3O-C6H4 (4d), p-(CH3)(2)N-C6H4 (4e)) were obtained in moderate yields from reactions of C-60 with aldehydes 2a-e and N-methylglycine (Prato reaction). In all these solvent-free reactions, 4a was found to be formed besides 4b-e, indicating that fullerenes can react with N-substituted glycines in the absence of aldehyde to give fulleropyrrolidines. For this novel reaction, a possible reaction mechanism involving an electron transfer process has been proposed. Intrigued by this observation, the dependence of the yield on the reagent ratio for the reaction of C-60 with paraformaldehyde and/or N-methylglycine was examined to search the optimal conditions. The reaction of C-70 with paraformaldehyde and/or N-methylglycine under HSVM conditions was also studied and was found to give the positional isomers of [70]fulleropyrrolidines. (C) 2002 Elsevier Science Ltd. All rights reserved.