2-amino-7,7-dimethyl-5-oxo-1-phenyl-4-(p-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile | 1373934-09-8

• 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-5-oxo-1-phenyl-4-(p-tolyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 2-Amino-1,4,5,6,7,8-hexahydro-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-1-phenylquinoline-3-carbonitrile；2-amino-7,7-dimethyl-4-(4-methylphenyl)-5-oxo-1-phenyl-6,8-dihydro-4H-quinoline-3-carbonitrile
• CAS: 1373934-09-8
• 化学式: C₂₅H₂₅N₃O
• 分子量: 383.493
• InChiKey: FZYOTIBBTWJEPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

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 0.25h， 生成 2-amino-7,7-dimethyl-5-oxo-1-phenyl-4-(p-tolyl)-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

• Crown ether complex cation ionic liquids: synthesis and catalytic applications for the synthesis of tetrahydro-4<i>H</i>-chromene and 1,4-dihydropyridine derivatives
  作者：Mehdi Abaszadeh、Mohammad Seifi

  DOI：10.1080/17415993.2017.1293058

  日期：2017.7.4

  ABSTRACT A series of crown ether complex cation ionic liquids (CECILs) are synthesized by crown ethers chelated with sodium benzenesulfonates, and used as a green and environmental catalyst, for the synthesis of tetrahydro-4H-chromene and 1,4-dihydropyridine derivatives by three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively

  摘要 冠醚与苯磺酸钠螯合合成了一系列冠醚络合阳离子离子液体（CECILs），作为一种绿色环保催化剂，用于三氢苯磺酸钠合成四氢-4H-色烯和1,4-二氢吡啶衍生物。 - 芳香醛和丙二腈分别与环状 β-二羰基或环状 β-烯氨基酮在 H2O/EtOH (1:1) 中在回流条件下的组分反应。CECILs作为一种绿色环保的催化剂，容易获得且稳定。此外，高转化率、短反应时间和更清洁的反应曲线是该方法的一些优点。图形概要
• 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。
• 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
• Ultrasound promotes one-pot synthesis of 1,4-dihydropyridine and imidazo[1,2-a]quinoline derivatives, catalyzed by ZnO nanoparticles
  作者：Mehdi Abaszadeh、Mohammad Seifi、Ali Asadipour

  DOI：10.1007/s11164-014-1624-7

  日期：2015.8

  Ultrasonic irradiation is being considered not only as a green approach but also as a powerful technique for the synthesis of 1,4-dihydropyridine and imidazo[1,2-a]quinoline derivatives. It can be carried out by using multicomponent reaction of cyclic enaminoketones, malononitrile, and aromatic aldehydes, in the presence of catalytic amounts of zinc oxide nanoparticles, in EtOH, at 80 °C. The preponderance of such a catalyst is due to its inexpensiveness, stability, and the potential of being easily obtained. Furthermore, high conversions, short reaction times, and cleaner reaction profiles are some of the advantages of this method.

  超声波辐照不仅被认为是一种绿色方法，而且还是一种合成 1,4-二氢吡啶和咪唑并[1,2-a]喹啉衍生物的强大技术。它可以在催化氧化锌纳米颗粒的存在下，在 80 ℃ 的乙醇中，通过环状烯酮酮、丙二腈和芳香醛的多组分反应来实现。这种催化剂的优势在于其低敏性、稳定性和易于获得的潜力。此外，高转化率、短反应时间和更清洁的反应曲线也是这种方法的一些优点。