(2S,5S)-2-carboxymethyl-5-(p-metoxyphenyl)pyrrolidino[3,4:25,8][70]fullerene | 1393577-28-0

• 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: (2S,5S)-2-carboxymethyl-5-(p-metoxyphenyl)pyrrolidino[3,4:25,8][70]fullerene
• CAS: 1393577-28-0
• 化学式: C₇₈H₉NO₂S
• 分子量: 1024.0
• InChiKey: AQNVUPWBCNDOAB-PCVWSXOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.2
• 重原子数：
  82.0
• 可旋转键数：
  2.0
• 环数：
  39.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  cis-2-carboxymethyl-5-(2-thiophenyl)pyrrolidino[3,4:25,8][70]fullerene 以 乙腈 为溶剂， 反应 48.0h， 以96%的产率得到
  参考文献：
  名称：

  Enantiospecific cis–trans Isomerization in Chiral Fulleropyrrolidines: Hydrogen-Bonding Assistance in the Carbanion Stabilization in H₂O@C₆₀

  摘要：

  The stereochemical outcome of cis-trans isomerization of optically pure [60], [70], and endohedral H2O@C60 fulleropyrrolidines reveals that the electronic nature of substituents, fullerene size, and surprisingly the incarcerated water molecule plays a crucial role in this rearrangement process. Theoretical DFT calculations are in very good agreement with the experimental findings. On the basis of the experimental results and computational calculations, a plausible reaction mechanism involving the hydrogen-bonding assistance of the inner water molecule in the carbanion stabilization of endofullerene is proposed.

  DOI：

  10.1021/ja5108854

文献信息

• Switching the Stereoselectivity: (Fullero)Pyrrolidines “a la Carte”
  作者：Enrique E. Maroto、Salvatore Filippone、Angel Martín-Domenech、Margarita Suarez、Nazario Martín

  DOI：10.1021/ja306105b

  日期：2012.8.8

  Stereodivergent syntheses of cis/trans pyrrolidino[3,4:1,2]fullerenes and endo/exo pyrrolidines are reported with high enantioselectivity levels. Fullerenes are revealed as a useful benchmark to develop suitable catalysts to control the stereochemical outcome and to shed light on the mechanism involved in the related 1,3-dipolar cycloaddition.