cis-1-(2,6-dimethyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-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-(2,6-dimethyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one
• 英文别名: 1-(2,6-dimethyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one；1-[(2R,4S)-2,6-dimethyl-1,2,3,4-tetrahydroquinolin-4-yl]azepan-2-one
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: RDVMGURSWRFMDH-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 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-乙烯基己内酰胺 、 乙烷,三氯氟- 在 三氯化锑 作用下， 以 乙腈 为溶剂， 反应 1.83h， 以88%的产率得到cis-1-(2,6-dimethyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one
  参考文献：
  名称：

  一锅药用重要的顺式-2-甲基-4-氨基取代的1,2,3,4-四氢喹啉

  摘要：

  简单合成具有医学重要性的顺式-2-甲基-4-氮杂泛-2-1-2-，1,2,3,4-四氢喹啉/顺式-9-（2-甲基1,2,3,4-四氢喹啉-4 -yl）-9 H-咔唑的报道。以三氯化锑为催化剂，乙腈为溶剂，通过亚氨基Diels-Alder反应，与苯胺和N-乙烯基己内酰胺/ N-乙烯基咔唑进行多组分一锅合成。NMR技术（2D）用于研究新合成化合物的区域和立体化学。产品的顺式非对映选择性是通过COZY和NOESY研究预测的。

  DOI：

  10.1002/cjoc.201100180

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。
• 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.
• Catalyst-free diastereoselective synthesis of 2-methyl-4-amino-1,2,3,4-tetrahydro-quinoline derivatives in water
  作者：Lin Wu、Ran Jiang、Jin-Ming Yang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tetlet.2013.03.091

  日期：2013.5

  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.