cis-1-(6-chloro-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-(6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one
• 英文别名: cis-1-(6-chloro-2-methyl-1,2,3,4-tetrahydroquinoline-4-yl)pyrrolidin-2-one；cis-1-(2-methyl-6-chloro-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；N-(6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-one；1-[(2R,4S)-6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
• 化学式: C₁₄H₁₇ClN₂O
• 分子量: 264.755
• InChiKey: GHQFYAUBXODWGT-RNCFNFMXSA-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：
  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 、 对氯苯胺 在 indium(III) chloride 作用下， 以 水 为溶剂， 反应 0.17h， 以93%的产率得到cis-1-(6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one
  参考文献：
  名称：

  InCl3/H2O催化一锅立体选择性合成cis-2-Methyl-4-amido-1,2,3,4-四氢喹啉衍生物

  摘要：

  摘要 在三氯化铟存在下，在水介质中，芳香胺与 N-乙烯基己内酰胺或 N-乙烯基吡咯烷酮反应，高效合成了各种顺式-2-甲基-4-酰胺基-1,2,3,4-四氢喹啉衍生物。良好的产量。这些 2,4-二取代的四氢尿啉表现出顺式非对映选择性。

  DOI：

  10.1080/00397911003650453

文献信息

• Efficient InCl₃/H₂O-Catalyzed One-Pot Stereoselective Synthesis of<i>cis</i>-2-Methyl-4-amido-1,2,3,4-tetrahydroquinoline Derivatives
  作者：P. Prabhakara Varma、Aswathnarayana Srinivasa、Kittappa M. Mahadevan

  DOI：10.1080/00397911003650453

  日期：2011.8

  Abstract Various cis-2-methyl-4-amido-1,2,3,4-tetrahydroquinoline derivatives were synthesized efficiently by reacting aromatic amines and N-vinyl caprolactam or N-vinyl pyrrolidone in the presence of indium trichloride in an aqueous medium in good to excellent yields. These 2,4-disubstituted tetrahydrouinolines showed cis diastereoselectivity.

  摘要 在三氯化铟存在下，在水介质中，芳香胺与 N-乙烯基己内酰胺或 N-乙烯基吡咯烷酮反应，高效合成了各种顺式-2-甲基-4-酰胺基-1,2,3,4-四氢喹啉衍生物。良好的产量。这些 2,4-二取代的四氢尿啉表现出顺式非对映选择性。
• FeCl₃-Catalyzed Synthesis of 2-Methyl-4-Substituted-1,2,3,4-Tetrahydroquinoline Derivatives by the Imino Diels-Alder Reaction
  作者：Ye Chen、Yong-Rok Lee

  DOI：10.5012/bkcs.2011.32.7.2485

  日期：2011.7.20
• Use of iodine doped polyaniline salt in the stereoselective synthesis of 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives
  作者：Rajender Boddula、Palaniappan Srinivasan

  DOI：10.1016/j.catcom.2012.11.002

  日期：2013.1

  Polyaniline-iodine salt is proved as a simple, efficient, versatile, recyclable and eco-friendly polymer based solid acid catalyst in the reaction between aromatic amines and N-vinyl pyrrolidone/N-vinyl caprolactam under solvent free condition. Polyaniline salts such as polyaniline-sulfate, polyaniline-hydrochloride and polyaniline-perchlorate are also catalyzing this reaction smoothly. (c) 2012 Elsevier B.V. All rights reserved.
• Simple entry to new 2-alkyl-1,2,3,4-tetrahydroquinoline and 2,3-dialkylquinoline derivatives using BiCl3-catalyzed three component reactions of anilines and aliphatic aldehydes in the presence (or lack) of N-vinyl amides
  作者：Vladimir V. Kouznetsov、Carlos M. Meléndez Gómez、Fernando A. Rojas Ruíz、Esther del Olmo

  DOI：10.1016/j.tetlet.2012.04.008

  日期：2012.6

  A general protocol for the simple and efficient synthesis of 2-alkyl-1,2,3,4-tetrahydroquinolines and 2,3-dialkylquinolines was reported. Synthetic protocol describes the one-pot preparation of these tetrahydroquinoline and quinoline products using the same reagents (aliphatic aldehydes and anilines) in the BiCl3-catalyzed multicomponent condensation process where the third component, N-vinyl amide is present. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 1-(2-Methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones from Anilines and<i>N</i>-Vinyl Pyrrolidin-2-one Through Imino Diels–Alder Reaction Using 4-Nitro Phthalic Acid as Catalyst
  作者：Aswathanarayana Srinivasa、Kittappa M. Mahadevan、Vijaykumar Hulikal

  DOI：10.1080/00397910802369653

  日期：2008.12.16

  Aryl amines react smoothly and efficiently with N-vinyl pyrrolidin-2-one in the presence of 4-nitro phthalic acid in acetonitrile to afford the corresponding 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones in good yields.