1-benzyl-5-(1H-indol-3-yl)pyrrolidin-2-one | 1119393-47-3

• 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-(1H-indol-3-yl)pyrrolidin-2-one
• CAS: 1119393-47-3
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: KFOSYPHFPZSUIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  558.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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-(1H-indol-3-yl)pyrrolidin-2-one 在 tetraphosphorus decasulfide 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (E)-1-benzyl-5-(1H-indol-3-yl)-2-nitromethylenepyrrolidine
  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-烯丙基苄胺 在 二氯(邻异丙氧基苯基亚甲基)(三环己基膦)钌 、 硼酸 、 三乙胺 作用下， 以 二氯甲烷 、 间二甲苯 为溶剂， 反应 21.0h， 生成 1-benzyl-5-(1H-indol-3-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

  摘要：

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

  DOI：

  10.1021/ol400654r

文献信息

• Enantioselective, Thiourea-Catalyzed Intermolecular Addition of Indoles to Cyclic N-Acyl Iminium Ions
  作者：Emily A. Peterson、Eric N. Jacobsen

  DOI：10.1002/anie.200902420

  日期：——

  Fair game for indoles, N‐acyl iminium ion intermediates underwent intermolecular addition by these nucleophiles under the catalysis of a chiral thiourea Schiff base derivative. A variety of functionalized indole frameworks were assembled with high enantioselectivity from simple precursors by this method (see scheme; TMS=trimethylsilyl; R=H, Me, vinyl, OMe, F, Cl, Br; R1=benzyl, methyl; n=1,2).

  吲哚的公平游戏，N-酰基亚胺离子中间体在手性硫脲席夫碱衍生物的催化下由这些亲核试剂进行分子间加成。通过这种方法从简单的前体以高对映选择性组装了各种功能化的吲哚骨架（参见方案；TMS=三甲基甲硅烷基；R=H、Me、乙烯基、OMe、F、Cl、Br；R 1 = 苄基、甲基；n = 1,2)。
• 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.
• Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein
  作者：Mette T. Petersen、Thomas E. Nielsen

  DOI：10.1021/ol400654r

  日期：2013.4.19

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.
• 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.