ethyl 4-(2,4-dichlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate | 33323-06-7

• 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: ethyl 4-(2,4-dichlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
• 英文别名: ethyl 4-(2,4-dichlorophenyl)-2-methyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 33323-06-7
• 化学式: C₁₉H₁₉Cl₂NO₃
• 分子量: 380.271
• InChiKey: IYCJXSKYYFLVJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 1,3-环己二酮 、 2,4-二氯苯甲醛 在 tetraethylammonium 2-(carbamoyl)benzoate 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以92%的产率得到ethyl 4-(2,4-dichlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  2-（氨基甲酰基）苯甲酸四乙铵作为双功能有机催化剂，用于一锅法合成Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物

  摘要：

  摘要已经开发了一种绿色，方便且环境友好的方法，该方法通过在2-乙基氨基甲酸酯苯甲酸四乙铵（一种有效的不含金属的双金属催化剂）存在下合成具有生物活性的Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物。在回流条件下，各种醛，乙酰乙酸乙酯或环状1,3-二羰基化合物和乙酸铵在EtOH中的一锅多组分反应。所提出的方法能够以直接的后处理和低成本的方法以良好至优异的产率和短的反应时间提供所需的产物。 图形概要

  DOI：

  10.1007/s00706-016-1666-1

文献信息

• Microwave-Assisted IBX-Mediated One-Pot Four-Component Synthesis of 4-Arylhexahydroquinoline Derivatives from Benzyl Alcohols: A Metal-Free Approach
  作者：D. Khan、Shaily、N. Maurya

  DOI：10.1134/s107042802304019x

  日期：2023.4

  Abstract An operationally convenient microwave-enhanced IBX-mediated one-pot multicomponent reaction has been proposed for the preparation of hexahydrohydoquinoline derivatives from benzyl alcohols, cyclic 1,3-diketones, ammonium acetate, and ethyl acetoacetate. The reaction is likely to involve the oxidation of benzyl alcohol into benzaldehyde and sequential reactions with other components. o-Iodoxybenzoic

  摘要 提出了一种操作方便的微波增强 IBX 介导的一锅多组分反应，用于从苯甲醇、环状 1,3-二酮、乙酸铵和乙酰乙酸乙酯制备六氢喹啉衍生物。该反应可能涉及苯甲醇氧化成苯甲醛以及与其他组分的连续反应。邻碘苯甲酸是一种容易获得的高价碘（V）试剂，被发现在生态友好的环境下对于这种转化非常有效。10 分钟内即可生产出各种取代的六氢喹啉衍生物，收率高达 96%。
• Hydromagnesite as an Efficient Recyclable Heterogeneous Solid Base Catalyst for the Synthesis of Flavanones, Flavonols and 1,4-Dihydropyridines in Water
  作者：U. Chinna Rajesh、Sunny Manohar、Diwan S. Rawat

  DOI：10.1002/adsc.201300555

  日期：2013.11.11

  AbstractA form of hydromagnesite (HM) with flower‐like thin‐sheet morphology was synthesized by an environmentally benign approach using simple conventional heating at moderate temperature without using any template in water as medium. The versatility of this HM catalyst was studied in the synthesis of flavanones, flavonols and the multicomponent synthesis of 1,4‐dihydropyridines in water. The recyclability of catalyst was studied for six times and there was no appreciable loss in its catalytic activity.magnified image
• Synthesis of MCM-41 supported cobalt (II) complex for the formation of polyhydroquinoline derivatives
  作者：Saurabh Sharma、Udai P. Singh、A.P. Singh

  DOI：10.1016/j.poly.2021.115102

  日期：2021.5
• POLYHYDROQUINOLINE COMPOUNDS AND DIHYDROPYRIDINE COMPOUNDS FOR INHIBITING BETA-AMYLOID PRODUCTION
  申请人：Mullan Michael J.

  公开号：US20100119599A1

  公开（公告）日：2010-05-13

  Provided are methods of treating or reducing the risk of developing beta-amyloid production, beta-amyloid deposition, beta-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of polyhydroquinoline and dihydropyridine compounds which decrease Abeta production in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of polyhydroquinoline and dihydropyridine compounds which decrease Abeta production in cells.
• Tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst for one-pot synthesis of Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives
  作者：Mahsa Yarhosseini、Shahrzad Javanshir、Mohammad G. Dekamin、Mohammad Farhadnia

  DOI：10.1007/s00706-016-1666-1

  日期：2016.10

  environment-friendly approach for the synthesis of biologically active Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives in the presence of tetraethylammonium 2-(carbamoyl)benzoate, as an effective bifunctional metal-free catalyst, has been developed via a one-pot multicomponent reaction of various aldehydes, ethyl acetoacetate or cyclic 1,3-dicarbonyl compounds, and ammonium acetate in EtOH

  摘要已经开发了一种绿色，方便且环境友好的方法，该方法通过在2-乙基氨基甲酸酯苯甲酸四乙铵（一种有效的不含金属的双金属催化剂）存在下合成具有生物活性的Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物。在回流条件下，各种醛，乙酰乙酸乙酯或环状1,3-二羰基化合物和乙酸铵在EtOH中的一锅多组分反应。所提出的方法能够以直接的后处理和低成本的方法以良好至优异的产率和短的反应时间提供所需的产物。 图形概要