N,N-diethyl-2-(9H-(C60-Ih)[5,6]fulleren-1-yl)propanamide | 151759-15-8

• 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,N-diethyl-2-(9H-(C60-Ih)[5,6]fulleren-1-yl)propanamide
• CAS: 151759-15-8
• 化学式: C₆₇H₁₅NO
• 分子量: 849.862
• InChiKey: ARAHCKQKWMBLEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  69
• 可旋转键数：
  4
• 环数：
  32.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-(9H-(C60-Ih)[5,6]fulleren-1-yl)propanamide 在 甲烷 作用下， 以 二硫化碳 为溶剂， 反应 360.0h， 以30%的产率得到
  参考文献：
  名称：

  活性炭作为富勒烯加合物氧化环化的试剂

  摘要：

  C 60与二乙基氨基丙炔的反应生成环丁烯加合物1，该环丁烯加合物1在酸水解后提供了一种容易的合成路线，形成富勒烯加合物2。随后涉及活性炭的氧化环化产生新型富勒烯内酯3。

  DOI：

  10.1016/s0040-4039(98)01527-5
• 作为产物：
  描述：

  N,N-二乙基丙酰胺 在 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 N,N-diethyl-2-(9H-(C60-Ih)[5,6]fulleren-1-yl)propanamide
  参考文献：
  名称：

  Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

  摘要：

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h

文献信息

• Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions
  作者：Yves Rubin、Padma S. Ganapathi、Andreas Franz、Yi-Zhong An、Wenyuan Qian、Reinhard Neier

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h

  日期：1999.11.5

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.
• Activated carbon as the reagent for the oxidative cyclization of fullerene adducts
  作者：Robert Bernstein、Christopher S. Foote

  DOI：10.1016/s0040-4039(98)01527-5

  日期：1998.9

  Reaction of C60 with diethylaminopropyne leads to cyclobutene adduct 1, which upon acid hydrolysis provides a facile synthetic route to fullerene adduct 2. Subsequent oxidative cyclization involving activated carbon yields the novel fullerene lactone 3.

  C 60与二乙基氨基丙炔的反应生成环丁烯加合物1，该环丁烯加合物1在酸水解后提供了一种容易的合成路线，形成富勒烯加合物2。随后涉及活性炭的氧化环化产生新型富勒烯内酯3。