2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-1-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

• 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: 2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-1-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-1-phenyl-6,8-dihydro-4H-quinoline-3-carbonitrile
• 化学式: C₂₄H₂₂FN₃O
• 分子量: 387.457
• InChiKey: JCPVHQJWKPLWLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 三乙烯二胺 、 四乙基溴化铵 作用下， 以 水 为溶剂， 反应 0.42h， 生成 2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-1-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Singh, Satish Kumar; Jena, Sambedan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 6, p. 821 - 824

  摘要：

  DOI：

文献信息

• Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media
  作者：Shijay Gao、Cheng Hsuan Tsai、Chi Tseng、Ching-Fa Yao

  DOI：10.1016/j.tet.2008.06.061

  日期：2008.9

  4H-Chromene and N-arylquinoline derivatives are obtained in good to excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.

  通过使用氟化四丁基铵（TBAF）进行简单，温和和有效的程序，可以高至极好的收率获得4 H- Chromene和N-芳基喹啉衍生物。
• Synthesis of N-Aryl-4-arylhexahydroquinoline Derivatives by Reaction of Cyclic Enaminones with Arylidenemalononitriles in DMSO
  作者：Takeshi Oriyama、Wei Han、Chika Inoue、Tsunaki Onizawa

  DOI：10.1055/s-0040-1705984

  日期：2021.4

  The reaction of cyclic enaminones with arylidenemalono­nitriles was carried out in the presence of 13X molecular sieves in dimethyl sulfoxide. Under these mild reaction conditions, various bioactive N-aryl-4-arylhexahydroquinoline derivatives were obtained in high yields without the necessity of using transition-metal catalyst, organobase, or reflux conditions.

  环状烯胺酮与芳基丙二腈的反应是在13X分子筛存在下于二甲基亚砜中进行的。在这些温和的反应条件下，无需使用过渡金属催化剂，有机碱或回流条件就可以高收率获得各种生物活性的N-芳基-4-芳基六氢喹啉衍生物。
• DBU-catalyzed expeditious and facile multicomponent synthesis of N-arylquinolines under microwave irradiation
  作者：Satish Kumar Singh、Krishna Nand Singh

  DOI：10.1007/s00706-011-0651-y

  日期：2012.5

  AbstractN-Arylquinoline derivatives are obtained in excellent yields by a rapid, easy, and efficient one-pot multicomponent reaction of aromatic aldehydes, 3-arylamino-5,5-dimethylcyclohex-2-enone, and active methylene compounds utilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst in ethanol under microwave irradiation. Graphical abstract

  摘要N-芳基喹啉衍生物可通过使用1,8-二氮杂双环与芳香醛，3-芳基氨基-5,5-二甲基环己-2-烯酮和活性亚甲基化合物进行快速，简便和有效的一锅多组分反应而以优异的收率获得[5.4.0]十一碳-7-烯（DBU）在微波辐射下作为乙醇中的催化剂。 图形概要
• Novel Biopolymer-Based Catalyst for the Multicomponent Synthesis of N-aryl-4-aryl-Substituted Dihydropyridines Derived from Simple and Complex Anilines
  作者：Giovanna Bosica、Roderick Abdilla

  DOI：10.3390/molecules29081884

  日期：——

  Lastly, this catalyst managed to afford an unprecedented product that was derived using an innovative technique—a combination of multicomponent reactions. Essentially, the product of our previously reported aza-Friedel–Crafts multicomponent reaction could itself be used as a reactant instead of aniline in the synthesis of more complex dihydropyridines.

  尽管 Hantzsch 合成已成为一种成熟的多组分反应方法十多年来，但其衍生物（即苯胺取代醋酸铵作为氮源）尚未得到深入研究。最近的研究表明，这种反应的产物N-芳基-4-芳基二氢吡啶（DHP）具有显着的抗癌活性。在这项研究中，我们使用一种无​​金属、温和、廉价、可回收、基于生物聚合物的多相催化剂（称为哌嗪）成功合成了多种 DHP（18 个例子，其中 8 个是新颖的）。在琼脂-琼脂凝胶中。此外，使用靛红代替醛作为反应物合成了此类二氢吡啶的另外 8 个实例（3 个新颖），产生螺连接结构。最后，这种催化剂成功地提供了一种前所未有的产品，该产品是使用创新技术（多组分反应的组合）衍生出来的。本质上，我们之前报道的氮杂-弗里德尔-克拉夫茨多组分反应的产物本身可以用作反应物，而不是苯胺来合成更复杂的二氢吡啶。
• Three-component green synthesis of N-arylquinoline derivatives in ionic liquid [Bmim+][BF4−]: reactions of arylaldehyde, 3-arylamino-5,5-dimethylcyclohex-2-enone, and active methylene compounds
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Hong Jiang、Chang-Sheng Yao、Shu-Jiang Tu

  DOI：10.1016/j.tet.2007.03.068

  日期：2007.5

  Three series of N-arylquinoline derivatives were synthesized by the three-component reactions of arylaidehyde, 3-arylamino-5,5-diinethyleyclohex-2-enone, and active methylene compounds including malononitrile, meldrum's acid, and 1,3-indenedione in ionic liquid [bmim(+)][BF4-] at 90 degrees C. (C) 2007 Elsevier Ltd. All rights reserved.