1-(1-(phenylamino)ethyl)pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(1-(phenylamino)ethyl)pyrrolidin-2-one
• 英文别名: 1-(1-Anilinoethyl)pyrrolidin-2-one；1-(1-anilinoethyl)pyrrolidin-2-one
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: QFTMQAMPRIUGSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-乙烯基吡咯烷酮 、 1-(1-(phenylamino)ethyl)pyrrolidin-2-one 以 水 为溶剂， 反应 24.0h， 以64%的产率得到cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl) pyrrolidin-2-one
  参考文献：
  名称：

  Catalyst-free diastereoselective synthesis of 2-methyl-4-amino-1,2,3,4-tetrahydro-quinoline derivatives in water

  摘要：

  A diastereoselective synthesis of 2-methyl-4-amino-1,2,3,4-tetrahydro-quinoline derivatives was achieved through the reaction of aromatic amines and tert-enamides in water under reflux conditions. The desired products could be obtained in moderate to excellent yields utilizing water as solvent without any catalyst or additive. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.03.091
• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 (E)-N-(4-methoxybenzylidene)aniline 在 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到1-(1-(phenylamino)ethyl)pyrrolidin-2-one
  参考文献：
  名称：

  N-芳基亚胺和 N-乙烯基内酰胺之间的阳离子自由基氮杂-狄尔斯-阿尔德反应：4-内酰胺-N-基四氢喹啉的简便合成

  摘要：

  N-芳基亚胺与 N-vinylpyrrolidin-2-one 或 N-vinylazepan-2-one 的环加成由三（4-溴苯基）六氯锑酸铵有效诱导，立体选择性地产生相应的 cis-2-aryl-4-(2-oxopyrrolidin- 1-yl)-或cis-2-aryl-4-(2-oxoazepan-l-yl)四氢喹啉衍生物，收率良好。

  DOI：

  10.1055/s-2006-942521

文献信息

• 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。
• Alkylation of aromatic amines by <i>tert</i>-enamides: Direct access to protected aminals
  作者：Azim Ziyaei Halimehjani、Mehri Goudarzi、Yazdanbakhsh Lotfi Nosood

  DOI：10.1080/00397911.2017.1363241

  日期：2017.11.2

  ABSTRACT Reaction of aromatic amines with tertiary enamides was performed in n-hexane in the presence of acetic acid as an inexpensive and green catalyst at room temperature. This protocol provides the protected aminals through Markovnikov addition reaction with high to excellent yields and regiospecificity. In addition, this procedure was expanded for the synthesis of aminals from commercially available

  摘要 芳香胺与叔烯酰胺的反应是在正己烷中，在乙酸作为廉价和绿色催化剂的存在下，在室温下进行的。该协议通过马尔科夫尼科夫加成反应提供了受保护的缩醛胺，具有高到极好的产率和区域特异性。此外，该程序还用于从市售磺胺类药物（如磺胺噻唑和磺胺苯甲酰胺）合成胺类。图形概要
• Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues
  作者：Ran Jiang、Hai-Yan Xu、Xiao-Ping Xu、Xue-Qiang Chu、Shun-Jun Ji

  DOI：10.1039/c1ob05546a

  日期：——

  Direct alkylation of indoles and amines by tertiary enamides for the synthesis of pharmaceutically active 2-oxo-1-pyrrolidine analogues was described. With only a 0.5 mol% catalyst loading, molecular iodine was demonstrated to be efficiently enough to promote the reaction under neat condition. Only Markovnikov addition product was obtained indicating that the reactions proceeded with excellent regioselectivity.

  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。
• A green approach for the one-pot multi-component synthesis of N-substituted γ, δ and ε-lactams involving C–N bond formation catalyzed by FeCl3
  作者：Venkatesan Sathesh、Munusamy Sathishkumar、Gunasekar Ramachandran、Ravindranath S. Rathore、Kulathu Iyer Sathiyanarayanan

  DOI：10.1039/c3ra44472d

  日期：——

  A green trend and efficient method for the synthesis of N-substituted γ, δ and ε-lactam derivatives has been developed through one pot multi-component reaction under environmentally benign reaction conditions using FeCl3 as a green catalyst with high atom economy. The present green synthetic protocol shows fascinating properties such as enhanced yield in solvent-free conditions, with high reaction rate, easy workup and absence of column chromatography and also avoids the use of ligands or additives. The versatility of the reaction has been ascertained by using various substituted benzaldehydes, anilines and homologues of lactams.

  以具有高原子经济性的 FeCl3 为绿色催化剂，在无害环境的反应条件下，通过一锅多组分反应合成 N-取代的δ、δ和δ-内酰胺衍生物，开发出了一种绿色、高效的方法。本绿色合成方案显示出令人着迷的特性，如在无溶剂条件下产量提高、反应速率高、操作简便、无需柱层析，还避免了配体或添加剂的使用。通过使用各种取代的苯甲醛、苯胺和内酰胺的同系物，我们确定了该反应的多功能性。
• Cation Radical Aza-Diels-Alder Reaction between <i>N</i>-Arylimines and <i>N</i>-Vinyllactams: A Facile Synthesis of 4-Lactam-<i>N</i>-yl Tetrahydroquinolines
  作者：Xiaodong Jia、Li Yang、Bing Han、Wei Zhang、Xiaoling Jin、Zhong-Li Liu

  DOI：10.1055/s-2006-942521

  日期：2006.9

  Cycloaddition of N-arylimines with N-vinylpyrrolidin-2-one or N-vinylazepan-2-one was efficiently induced by tris(4-bromophenyl)aminium hexachloroantimonate producing stereoselectively the corresponding cis-2-aryl-4-(2-oxopyrrolidin-1-yl)- or cis-2-aryl-4-(2-oxoazepan-l-yl)tetrahydroquinoline derivative in good yields.

  N-芳基亚胺与 N-vinylpyrrolidin-2-one 或 N-vinylazepan-2-one 的环加成由三（4-溴苯基）六氯锑酸铵有效诱导，立体选择性地产生相应的 cis-2-aryl-4-(2-oxopyrrolidin- 1-yl)-或cis-2-aryl-4-(2-oxoazepan-l-yl)四氢喹啉衍生物，收率良好。