1-(1-(5-bromo-1H-indol-3-yl) ethyl)pyrrolidin-2-one | 1257640-64-4

• 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-(1-(5-bromo-1H-indol-3-yl) ethyl)pyrrolidin-2-one
• 英文别名: 1-(1-(5-bromo-1H-indol-3-yl)ethyl)pyrrolidin-2-one；1-[1-(5-bromo-1H-indol-3-yl)ethyl]pyrrolidin-2-one
• CAS: 1257640-64-4
• 化学式: C₁₄H₁₅BrN₂O
• 分子量: 307.19
• InChiKey: PAWMENBSAVVNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 5-溴吲哚 在 碘 作用下， 反应 2.0h， 以87%的产率得到1-(1-(5-bromo-1H-indol-3-yl) ethyl)pyrrolidin-2-one
  参考文献：
  名称：

  Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues

  摘要：

  本文报道了利用叔烯胺酯直接对吲哚和胺进行烷基化反应，合成药理活性2-氧代-1-吡咯烷类似物的方法。实验表明，在无溶剂条件下，仅需0.5 mol%的催化剂负载量，分子碘即可高效促进反应进行。产物仅为Markovnikov加成物，表明反应具有极高的区域选择性。

  DOI：

  10.1039/c1ob05546a

文献信息

• FeCl₃-promoted alkylation of indoles by enamides
  作者：Tianmin Niu、Lehao Huang、Tianxing Wu、Yuhong Zhang

  DOI：10.1039/c0ob00709a

  日期：——

  An efficient iron-promoted alkylation of indoles with enamides has been accomplished under mild reaction conditions. The reaction proceeded with remarkable regioselectivity leading exclusively to substitution by indoles at α-position of enamides.

  在温和的反应条件下，利用铁催化的吲哚与烯酰胺的烷基化反应已经高效完成。该反应表现出显著的区域选择性，结果仅在烯酰胺的α位点上发生吲哚的取代。
• Friedel-Crafts Alkylation of Indoles by tert-Enamides in Acetic Acid
  作者：Xiao-Ping Xu、Shun-Jun Ji、Ying Zhang、Jing Jiang、Xue-Qiang Chu、Ran Jiang、Dan-Hua Li

  DOI：10.1055/s-0031-1290605

  日期：2012.3

  In acetic acid, Friedel-Crafts alkylation of indoles by tert-enamides proceeded effectively in the absence of any catalyst to afford the pharmacologically and biologically active 2-oxo-1-pyrrolidine derivatives in moderate to good yields. The mechanistic study based on the NMR and HRMS analysis shows that the reaction was promoted by acid catalysis. The hydrogen-bond interaction between tert-enamides and AcOH may also be responsible for the reaction.

  在乙酸中，Friedel-Crafts 烷基化反应能够在不使用任何催化剂的情况下，通过叔烯酰胺有效地进行吲哚的烷基化，以中等至良好的产率获得具有药理学和生物学活性的2-氧代-1-吡咯烷衍生物。基于核磁共振（NMR）和高分辨质谱（HRMS）的机理研究表明，反应受到酸催化的促进作用。叔烯酰胺与乙酸之间的氢键相互作用也可能是反应的推动因素之一。
• Recyclable NaHSO4 catalyzed alkylation of tert-enamides with indoles or amines in water: facile construction of pharmaceutically analogous bis-alkaloid scaffolds
  作者：Xue-Qiang Chu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c3ra40833g

  日期：——

  An efficient sodium hydrogen sulfate catalyzed alkylation of indoles or amines with tertiary enamides has been accomplished in water, affording the pharmacologically and biologically active 2-oxo-1-pyrrolidine derivatives in moderate to excellent yields. The key to our success is the use of NaHSO4 as a low loading, inexpensive, green and recyclable catalyst and the reactions could be scaled up to gram level.

  高效硫酸氢钠催化吲哚或胺与三级烯胺酯在水相中的烷基化反应得以实现，从而在中等至优异的收率下获得药理学和生物活性相关的2-氧代-1-吡咯烷衍生物。我们成功的关键在于使用低负载量、经济实惠、环保且可回收的NaHSO4作为催化剂，并且这些反应可以放大至克级规模。
• Triarylaminium salt facilitated Friedel–Crafts reaction of indoles with enamides and vinyl ethers
  作者：Congde Huo、Lisheng Kang、Xiaolan Xu、Xiaodong Jia、Xicun Wang、Haisheng Xie、Yong Yuan

  DOI：10.1016/j.tetlet.2013.12.055

  日期：2014.1

  available stable radical cation triarylaminium salt can be used as an efficient initiator for Friedel–Crafts reaction of indoles with enamides to regioselectively construct complex indole derivatives and for double Friedel–Crafts reaction of indoles with vinyl ethers to offer 3,3′-Bis(indolyl)alkane derivatives. The ready availability of the starting materials and the usefulness of the products make this

  市售的稳定自由基阳离子三芳基铵盐可以用作吲哚与酰胺类化合物的Friedel-Crafts反应以选择性地构建复杂的吲哚衍生物的有效引发剂，以及吲哚与乙烯基醚的双重Friedel-Crafts反应以提供3,3'-Bis（）的有效引发剂。吲哚基）烷烃衍生物。起始材料的随时可用和产品的实用性使该策略具有吸引力。
• Ferric(III) Nitrate: An Efficient Catalyst for the Regioselective Friedel-Crafts Reactions of Indoles and tert-Enamides in Water
  作者：Ran Jiang、Xiao-Jin Wu、Xu Zhu、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1002/ejoc.201000994

  日期：2010.11

  The ferric nitrate catalyzed Friedel–Crafts reactions of various indoles and tertiary enamides, which proceed in water at room temperature, are demonstrated for an efficient, atom-economical and environmentally friendly route to produce indole derivatives under mild conditions. Based on experimental data and mechanistic studies, the iron(III) ion was found to activate the electron-rich C=C bond with

  硝酸铁催化的各种吲哚和叔烯酰胺在室温下在水中进行的弗瑞德-克来福特反应被证明是一种在温和条件下生产吲哚衍生物的有效、原子经济和环境友好的途径。根据实验数据和机理研究，发现铁 (III) 离子在催化过程中与羰基协同激活富电子的 C=C 键。