1,6-二甲基-2,3-二氢喹啉-4-酮 | 959699-02-6

• 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: 1,6-二甲基-2,3-二氢喹啉-4-酮
• 英文名称: 1,6-dimethyl-2,3-dihydro-1H-quinolin-4-one
• 英文别名: 1,6-dimethyl-2,3-dihydroquinolin-4(1H)-one；1,6-dimethyl-2,3-dihydroquinolin-4-one
• CAS: 959699-02-6
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: GSDJEBMYWQSYKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-二甲基-2,3-二氢喹啉-4-酮 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以62%的产率得到2,10-dimethyl-10H-acridin-9-one
  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
• 作为产物：
  描述：

  3-溴-N-(4-甲基苯基)丙酰胺 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， 反应 2.0h， 生成 1,6-二甲基-2,3-二氢喹啉-4-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

• Control over the Chemoselectivity of Pd-Catalyzed Cyclization Reactions of (2-Iodoanilino)carbonyl Compounds
  作者：Daniel Solé、Israel Fernández、Miguel A. Sierra

  DOI：10.1002/chem.201102811

  日期：2012.5.29

  The factors that control the chemoselectivity of palladium‐catalyzed cyclization reactions of (2‐iodoanilino)carbonyl compounds have been explored by an extensive experimental computational (DFT) study. It was found that the selectivity of the process, that is, the formation of fused six‐ versus five‐membered rings, can be controlled by the proper selection of the initial reactant, reaction conditions

  通过广泛的实验计算（DFT）研究已经探索了控制钯催化（2-碘代苯胺基）羰基化合物的化学选择性的因素。结果发现，该工艺的选择性，即，稠合的六元相对于五元环，可以通过初始反应物，反应条件和添加剂的适当选择被控制的形成。因此，酯或酰胺产生通过亲核加成过程酮，而另外的PhO的-离子通过α-芳基化反应导致二氢吲哚的形成。相反，在苯酚存在下，相应的酮反应物产生两种反应产物的混合物，其比例取决于所用的碱。这些过程的结果可以通过形成常见的四元的palladacycle中间体来解释，从该中间体中发生竞争性亲核加成和α-芳基化反应。苯酚在此过程中的显着作用使α-芳基化反应更容易，促进了烯醇配合物的形成，烯醇配合物通过烯醇部分的羟基与苯氧基配体的氧原子之间的分子内氢键得以稳定。而且，
• 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
• Intramolecular Pd(0)-Catalyzed Reactions of β-(2-Iodoanilino) Carboxamides: Enolate Arylation and Nucleophilic Substitution at the Carboxamide Group
  作者：Daniel Solé、Olga Serrano

  DOI：10.1021/jo8020715

  日期：2008.12.5

  Two different reaction pathways, the enolate arylation and the acylation of the aryl halide, can be promoted by a Pd(0) catalyst starting from beta-(2-iodoanilino) carboxamides. The intramolecular acylation of beta-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a sigma-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.
• 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.