6-甲氧基-1-甲基-2,3-二氢-4-喹啉酮 | 3954-50-5

• 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
• 中文名称: 6-甲氧基-1-甲基-2,3-二氢-4-喹啉酮
• 英文名称: 6-methoxy-1-methyl-2,3-dihydro-1H-quinolin-4-one
• 英文别名: 6-Methoxy-1-methyl-2,3-dihydro-4-chinolon；6-methoxy-1-methyl-2,3-dihydroquinolin-4(1H)-one；6-methoxy-1-methyl-2,3-dihydroquinolin-4-one
• CAS: 3954-50-5
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD09035327
• 分子量: 191.23
• InChiKey: VVMQFOOLHMRQTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲氧基-1-甲基-2,3-二氢-4-喹啉酮 在 吡啶 、 氨 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 28.0h， 生成 6-methoxy-1-methyl-3,4-dihydro-2H-quinolin-4-amine
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056
• 作为产物：
  描述：

  3-bromo-N-(4-methoxyphenyl)propionamide 在 三氟甲磺酸 、 sodium hydride 、 sodium t-butanolate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 6-甲氧基-1-甲基-2,3-二氢-4-喹啉酮
  参考文献：
  名称：

  Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

  摘要：

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

  DOI：

  10.1021/jo3011073

文献信息

• A Facile and Expeditious Synthesis of Cryptosanguinolentines
  作者：Dalip Kumar、Maruthi Kumar. N.、V. S. Rao

  DOI：10.1246/cl.2009.156

  日期：2009.2.5

  A simple and efficient synthesis of naturally occurring cryptosanguinolentines is described. Neat reaction of easily accessible 1-methyl-1,2,3,4-tetrahydroquinolin-4-ones and aryl hydrazines in the presence of p-toluenesulfonic acid at 100 °C rapidly afforded cryptosanguinolentines in very good yields.

  本文描述了天然存在的隐血素类化合物的一种简单有效的合成方法。在100°C下，在四甲基苯磺酸存在下，易得的1-甲基-1,2,3,4-四氢喹啉-4-酮和芳基肼的简单反应迅速产生了隐血素类化合物，且收率很高。
• Palladium-Catalyzed Intramolecular Nucleophilic Substitution at the Alkoxycarbonyl Group
  作者：Daniel Solé、Olga Serrano

  DOI：10.1002/anie.200702176

  日期：2007.9.24
• Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
  作者：Robert G. Schmidt、Erol K. Bayburt、Steven P. Latshaw、John R. Koenig、Jerome F. Daanen、Heath A. McDonald、Bruce R. Bianchi、Chengmin Zhong、Shailen Joshi、Prisca Honore、Kennan C. Marsh、Chih-Hung Lee、Connie R. Faltynek、Arthur Gomtsyan

  DOI：10.1016/j.bmcl.2011.01.056

  日期：2011.3

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.
• Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones
  作者：Yuesi Fang、Donald C. Rogness、Richard C. Larock、Feng Shi

  DOI：10.1021/jo3011073

  日期：2012.7.20

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.