cis-1-(2-methyl-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-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-azepan-2-one
• 英文别名: cis-1-(2-methyl-1,2,3,4-tetrahydroquinoline-4-yl)azepan-2-one；cis-2-methyl-4-(2-oxoazepan-1-yl)-1,2,3,4-tetrahydroquinoline；cis-1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one；1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)azepan-2-one；1-[(2R,4S)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]azepan-2-one
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: AJOXALUTKXLGMS-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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 、 苯胺 在 三氯化锑 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以86%的产率得到cis-1-(2-methyl-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。
• One Pot Synthesis of Medicinally Important cis-2-Methyl-4-amino substituted-1,2,3,4-tetrahydroquinolines
  作者：Kumar H. C. Kiran、K. M. Mahadevan、Varma P. Prabhakara、A. Srinivasa

  DOI：10.1002/cjoc.201100180

  日期：2012.3

  A simple synthesis of medicinally important cis‐2‐methyl‐4‐azapan‐2‐one‐1,2,3,4‐tetrahydroquinolines/cis‐9‐(2‐methyl‐1,2,3,4‐tetrahydroquinolin‐4‐yl)‐9H‐carbazole was reported. Multicomponent one pot synthesis with anilines and N‐vinylcaprolactam/N‐vinyl carbazole via imino Diels‐Alder reaction by using antimony trichloride as catalyst and acetonitrile as solvent was employed. NMR technique (2D) was

  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。
• 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。
• 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.