cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
• 英文别名: 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: LHFKTMHOXRRTJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基吡咯烷酮 、 苯胺 在 copper dipyridine dichloride 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one
  参考文献：
  名称：

  Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride

  摘要：

  在对位取代苯胺与 N-乙烯基吡咯烷酮、N-乙烯基咔唑和 N-乙烯基己内酰胺在乙腈中的亚氨基 Diels-Alder 反应中，首次使用二氯化吡啶铜（CuPy2Cl2）作为高效且可重复使用的催化剂，得到相应的 2-甲基-4-取代-1,2,3,4-四氢喹啉衍生物，收率极高且纯度良好。这些产品通过傅立叶变换红外光谱、1H NMR、13C NMR、质谱和元素分析进行了表征。

  DOI：

  10.1139/v10-016

文献信息

• Grinding and Milling: Two Efficient Methodologies in the Solvent-Free Phosphomolybdic Acid-Catalyzed and Mechanochemical Synthesis of<i>cis</i>-4-Amido-<i>N</i>-yl-2-methyl-tetrahydroquinolines
  作者：Vladimir V. Kouznetsov、Diego R. Merchán-Arenas、Carlos A. Martínez-Bonilla、Mario A. Macías、Pascal Roussel、Gilles H. Gauthier

  DOI：10.5935/0103-5053.20160117

  日期：——

  The ball-milling process of ABB' Povarov reaction through mechano-chemical activation with phosphomolybdic acid (PMA) as heteropolyacid (HPA) catalyst, was first time explored. The developed high speed vibratory ball milling (HSVBM) green method offers simple and efficient diastereoselective synthesis of cis-2,4-disubstituted tetrahydroquinolines in good to excellent yields (56-76%).
• Phosphotungstic Acid: An Efficient Catalyst for Synthesis of 2-Substituted Tetrahydroquinoline via Imino Diels–Alder Reaction and Fluorescent Studies
  作者：Kavitha C. S. Achar、Kallappa M. Hosamani、Harisha R. Seetharamareddy

  DOI：10.1080/00397910903531672

  日期：2010.12.21

  For the first time Phosphotungstic acid (PTA), is used as a some new catalyst for the synthesis of tetrahydroquinoline derivatives with high yields is described. PTA a heterogeneous catalyst is inexpensive, easily available, eco-friendly, water soluble, recoverable, stable to aqueous reaction conditions and further more, these 2-methyl tetrahydroquinoline derivatives shows a remarkable fluorescence property.
• Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride
  作者：C. S. Kavitha、K. M. Hosamani、R. S. Harisha

  DOI：10.1139/v10-016

  日期：2010.5

  For the first time, copper dipyridine dichloride (CuPy₂Cl₂) is used as an efficient and reusable catalyst for the imino Diels–Alder reaction of para-substituted anilines with N-vinylpyrrolidinone, N-vinylcarbazole, and N-vinylcaprolactam in acetonitrile to afford the corresponding 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives in excellent yields with good purity. The products were characterized by FTIR,¹H NMR,¹³C NMR, MS, and elemental analysis.

  在对位取代苯胺与 N-乙烯基吡咯烷酮、N-乙烯基咔唑和 N-乙烯基己内酰胺在乙腈中的亚氨基 Diels-Alder 反应中，首次使用二氯化吡啶铜（CuPy2Cl2）作为高效且可重复使用的催化剂，得到相应的 2-甲基-4-取代-1,2,3,4-四氢喹啉衍生物，收率极高且纯度良好。这些产品通过傅立叶变换红外光谱、1H NMR、13C NMR、质谱和元素分析进行了表征。