2-amino-7,7-dimethyl-4-(4-nitrophenyl)-5-oxo-1-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile | 476483-61-1

• 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-7,7-dimethyl-4-(4-nitrophenyl)-5-oxo-1-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 2-amino-7,7-dimethyl-4-(4-nitrophenyl)-5-oxo-1-phenyl-6,8-dihydro-4H-quinoline-3-carbonitrile
• CAS: 476483-61-1
• 化学式: C₂₄H₂₂N₄O₃
• 分子量: 414.464
• InChiKey: PTHWCHSYARYNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 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：
  116
• 氢给体数：
  1
• 氢受体数：
  6

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 0.5h， 生成 2-amino-7,7-dimethyl-4-(4-nitrophenyl)-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。
• One‐pot synthesis of 1,4‐dihydropyridines and <i>N</i> ‐arylquinolines in the presence of copper complex stabilized on MnFe ₂ O ₄ (MFO) as a novel organic–inorganic hybrid material and magnetically retrievable catalyst
  作者：Najmieh Ahadi、Akbar Mobinikhaledi、Mohammad Ali Bodaghifard

  DOI：10.1002/aoc.5822

  日期：2020.10

  The prepared organic–inorganic hybrid material was successfully used as an efficient and recoverable catalyst for the synthesis of 1,4‐dihydropyridines and N‐arylquinolines under mild and green reaction conditions. The results showed that the catalyst exhibited excellent catalytic activity under optimum reaction conditions and the desired products were obtained in good to excellent yields. The new

  在这项工作中，提出了基于席夫碱封装在二氧化硅层中的锰铁氧体纳米粒子的功能化以及随后引入铜的非均相催化剂的设计和合成。通过使用傅立叶变换红外光谱，X射线粉末衍射，场发射扫描电子显微镜，透射电子显微镜，能量色散X射线光谱，差示热重量分析，振动样品磁强分析和感应耦合等离子体来表征合成的混合材料光学发射光谱技术。制备的有机-无机杂化材料已成功用作合成1,4-二氢吡啶和N的有效且可回收的催化剂-芳基喹啉在温和和绿色的反应条件下。结果表明，该催化剂在最佳反应条件下表现出优异的催化活性，并且以良好至优异的产率获得了所需的产物。通过傅立叶变换红外光谱，1 H NMR和碳，氢和氮（CHN）分析的元素分析对新型1,4-二氢吡啶和N-芳基喹啉进行了表征。催化剂可重复使用性的研究证实，该催化剂可循环使用五次，但催化活性略有下降，铜的浸出可忽略不计。
• 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
• An efficient one-pot, three-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione and quinoline-3-carbonitrile derivatives from enaminones
  作者：Shu-Jiang Tu、Bo Jiang、Run-Hong Jia、Jun-Yong Zhang、Yan Zhang、Chang-Sheng Yao、Feng Shi

  DOI：10.1039/b607575d

  日期：——

  An efficient one-pot, three-component method for the preparation of indeno[1,2-b]quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione and various multi-substituted quinoline-3-carbonitrile derivatives has been developed through the Michael addition to enaminones, which was achieved by both microwave irradiation and conventional heating.

  一种高效的一锅三组分方法，用于制备茚并[1,2-b]喹啉-9,11（6H，10H）-二酮，-1啶-1,8（2H，5H）-二酮和多种通过对烯胺酮的迈克尔加成反应已经开发了取代的喹啉-3-腈衍生物，这是通过微波辐射和常规加热实现的。
• Combinatorial Library Synthesis of N-arylquinoline Derivatives in Aqueous Medium
  作者：Adeleh Moshtaghi Zonouz、Mina Raeisolsadati Oskouei

  DOI：10.1002/jccs.201200359

  日期：2013.3

  N‐aryl quinoline derivatives have been prepared by sequential one‐pot reaction of dimedone, aniline, malononitrile and arylaldehydes. The reactions were performed in two different conditions, refluxing in ethanol without catalyst and heating in ethanol/water (1:1) in the presence of imidazole as an organocatalyst. Use of organocatalyst causes shorter reaction times and higher yields.

  N-芳基喹啉衍生物是通过二甲酮，苯胺，丙二腈和芳醛的顺序一锅反应制备的。反应在两种不同条件下进行，在没有催化剂的情况下在乙醇中回流，以及在咪唑作为有机催化剂的存在下在乙醇/水（1：1）中加热。使用有机催化剂可缩短反应时间并提高产率。