1-benzyl-5-(2-p-tolyl-1H-indol-3-yl)pyrrolidin-2-one | 1119393-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-benzyl-5-(2-p-tolyl-1H-indol-3-yl)pyrrolidin-2-one
• 英文别名: 1-benzyl-5-[2-(4-methylphenyl)-1H-indol-3-yl]pyrrolidin-2-one
• CAS: 1119393-48-4
• 化学式: C₂₆H₂₄N₂O
• 分子量: 380.489
• InChiKey: ACLYNQDUKLGXFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  637.2±55.0 °C(predicted)
• 密度：
  1.216±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-(2-p-tolyl-1H-indol-3-yl)pyrrolidin-2-one 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 C₂₇H₂₇N₂S⁽¹⁺⁾*I^(1-)
  参考文献：
  名称：

  Condensations based on 5-(indol-3-yl)-pyrrolidin-2-thiones

  摘要：

  AbstractNew activated indolylpyrrolidones—their methylthiopyrrolinium salts—in the reactions with several CH‐acids were studied. 2‐Nitromethylene‐ and 2‐dicyanomethyleneindolylpyrrolidines were obtained from 5‐indolyl‐2‐methylthiopyrrolinium salts with good yields. The reduction in these nitro compounds yields the respective aminomethylpyrolidines. The rigid structure of the starting compounds has significant stereoelectronic requirements of nucleophilic agents.

  DOI：

  10.1002/hc.21451
• 作为产物：
  描述：

  N-苄基琥珀酰胺酸 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 24.0h， 生成 1-benzyl-5-(2-p-tolyl-1H-indol-3-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents

  摘要：

  The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.

  DOI：

  10.1007/s10593-011-0655-x

文献信息

• Reduction of 5-(indol-3-yl)pyrrolidin-2-ones
  作者：Andrey V. Sadovoy、Vita N. Nikitina、Victor B. Rybakov、Konstantin A. Kochetkov、Lyudmila A. Sviridova

  DOI：10.1007/s10593-016-1832-8

  日期：2016.1

  The reduction of activated 5-(indol-3-yl)pyrrolidin-2-ones leading to a mixture of the respective indolyl pyrrolidines and their borane complexes, as well as several other transformations indicate that the electrophilicity of carbonyl group in 5-indolylpyrrolidin-2-ones is significantly decreased.

  活化的5-（吲哚-3-基）吡咯烷丁-2-酮的还原导致各自的吲哚基吡咯烷及其硼烷络合物的混合物，以及其他一些转化反应表明5-吲哚基吡咯烷丁-中羰基的亲电子性2位明显减少。
• Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents
  作者：A. V. Sadovoy、A. E. Kovrov、G. A. Golubeva、L. A. Sviridova

  DOI：10.1007/s10593-011-0655-x

  日期：2011.1

  The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.
• Condensations based on 5-(indol-3-yl)-pyrrolidin-2-thiones
  作者：Andrey V. Sadovoy、Veronica V. Kattsyna、Polina S. Protopopova、Yulia V. Nelyubina、Alexander A. Pavlov、Konstantin A. Kochetkov、Lyudmila A. Sviridova

  DOI：10.1002/hc.21451

  日期：2018.7

  AbstractNew activated indolylpyrrolidones—their methylthiopyrrolinium salts—in the reactions with several CH‐acids were studied. 2‐Nitromethylene‐ and 2‐dicyanomethyleneindolylpyrrolidines were obtained from 5‐indolyl‐2‐methylthiopyrrolinium salts with good yields. The reduction in these nitro compounds yields the respective aminomethylpyrolidines. The rigid structure of the starting compounds has significant stereoelectronic requirements of nucleophilic agents.