5‐(4‐chlorophenyl)‐8,8‐dimethyl‐7,8,9,10‐tetrahydropyrimido[4,5‐b]quinoline‐2,4,6(1H,3H,5H)‐trione | 22281-33-0

• 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: 5‐(4‐chlorophenyl)‐8,8‐dimethyl‐7,8,9,10‐tetrahydropyrimido[4,5‐b]quinoline‐2,4,6(1H,3H,5H)‐trione
• 英文别名: 5-(4-chlorophenyl)-8,8-dimethyl-7,8,9,10-tetrahydro-pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione；5-(chlorophenyl)-8,8-dimethyl-7,8,9,10-tetrahydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione；5-(4-chloro-phenyl)-8,8-dimethyl-5,8,9,10-tetrahydro-1H,7H-pyrimido[4,5-b]quinoline-2,4,6-trione；Cambridge id 6618385；5-(4-chlorophenyl)-8,8-dimethyl-5,7,9,10-tetrahydro-1H-pyrimido[4,5-b]quinoline-2,4,6-trione
• CAS: 22281-33-0
• 化学式: C₁₉H₁₈ClN₃O₃
• 分子量: 371.823
• InChiKey: AZEKVQYZYVLLHG-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 4-氯苯甲醛 、 3-氨基-5,5-二甲基-2-环己烯-1-酮 在 哌啶 作用下， 以 水 为溶剂， 反应 1.0h， 以83%的产率得到5‐(4‐chlorophenyl)‐8,8‐dimethyl‐7,8,9,10‐tetrahydropyrimido[4,5‐b]quinoline‐2,4,6(1H,3H,5H)‐trione
  参考文献：
  名称：

  Rapid and efficient synthesis of fused heterocyclic pyrimidines under ultrasonic irradiation

  摘要：

  Some fused heterocyclic pyrimidines have been synthesized in high yields using ultrasound irradiation in a one-pot, three-component and efficient process by condensation reaction of barbituric acids, aldehydes and a series of enamines in water. Prominent among the advantages of this new method are operational simplicity, good yields in short reaction times and easy work-up procedures employed. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.07.002

文献信息

• A One-pot, Efficient Synthesis of Polyfunctionalized Pyrido[2,3-<i>d</i>]pyrimidines and Uncyclized Adducts by Aldehydes, 1,3-Dicarbonyl Compounds, and 6-Aminouracils
  作者：Guo-ping Lu、Chun Cai

  DOI：10.1002/jhet.1704

  日期：2014.11

  A one‐pot, efficient protocol for the synthesis of polyfunctionalized pyrido[2,3‐d]pyrimidines and uncyclized adducts by 6‐aminouracils in poly(ethylene glycol) 200/H2O or AcOH was described. An interesting family of pyrido[2,3‐d]pyrimidines and uncyclized adducts bearing fused pharmacological active units are prepared. The reaction is free of toxic solvents and catalysts, has simple workup procedure

  描述了一种在6-乙二醇尿嘧啶在聚（乙二醇）200 / H 2 O或AcOH中由6-氨基尿嘧啶合成多官能化吡啶并[2,3- d ]嘧啶和未环化加合物的有效方法。制备了一个有趣的吡啶并[2,3- d ]嘧啶家族和带有稠合药理活性单元的未环加合物。该反应不含有毒溶剂和催化剂，后处理步骤简单，原子经济性高，使其更环保，适合大规模操作。
• Green and rapid synthesis of dihydropyrimido [4,5‐ <i>b</i> ]quinolinetrione derivatives using CoFe ₂ O ₄ @PPA as high efficient solid acidic catalyst under ultrasonic irradiation
  作者：Leila Moradi、Pegah Mahdipour

  DOI：10.1002/aoc.4996

  日期：2019.8

  A new high efficient and green protocol for the preparation of dihydropyrimido[4,5‐b]quinolinetrione derivatives using magnetically solid acid catalyst was presented. High performance solid acid catalyst was prepared through a three‐step reaction. Firstly, CoFe2O4 nano particles were synthesized using co‐precipitation method. In second step, CoFe2O4 nano particles were coated with SiO2 shell through

  提出了一种使用磁性固体酸催化剂制备二氢嘧啶基[4,5- b ]喹啉三酮衍生物的新型高效绿色方案。通过三步反应制备了高性能固体酸催化剂。首先，采用共沉淀法合成了CoFe 2 O 4纳米颗粒。在第二步骤中，通过用原硅酸四乙酯（CoFe 2 O 4 @SiO 2）处理，用SiO 2壳涂覆CoFe 2 O 4纳米颗粒。最后，用多磷酸（CoFe）对CoFe 2 O 4 @SiO 2进行了改性。2 O 4 @SiO 2 / PPA）。使用FTIR，VSM，TEM，FESEM，EDX对绿色可重复使用的催化剂进行了详细表征，并用作合成二氢嘧啶基[4,5- b ]喹啉三酮衍生物的催化剂。在绿色，有效和温和的条件下，在超声辐射下进行反应，并以高至极好的收率获得了产物。该方法具有绿色环保的条件，反应时间短，产物收率高，而且易于操作。
• Efficient and green synthesis of dihydropyrimido[4,5‐ <i>b</i> ]quinolinetriones using MWCNTs@TEPA/Co (II) as a novel and eco‐friendly catalyst
  作者：Hakimeh Saeidiroshan、Leila Moradi

  DOI：10.1002/aoc.5732

  日期：2020.9

  A new heterogeneous nanocatalyst [MWCNTs@TEPA/Co (II)] was successfully prepared using multiwall carbon nanotubes (MWCNTs) as a suitable and efficient support for covalent anchoring of tetraethylene pentaamine (TEPA)/Co (II). The new heterogeneous catalyst was prepared through an easy and applicable method, and characterized by various techniques such as Fourier transform‐infrared, thermogravimetric

  使用多壁碳纳米管（MWCNT）成功地制备了新型多相纳米催化剂[MWCNTs @ TEPA / Co（II）]，作为四乙烯五胺（TEPA）/ Co（II）共价锚固的合适有效载体。新型非均相催化剂是通过一种简便且适用的方法制备的，并通过多种技术进行了表征，例如傅立叶变换红外，热重分析，能量色散X射线光谱，绘图，场发射扫描电子显微镜，电感耦合等离子体光学发射光谱法和Brunauer-Emmett-Teller。合成催化剂可有效地用于制备二氢嘧啶基[4,5- b通过热条件下巴比妥酸，二甲酮，芳基醛和胺的四组分反应生成]喹啉三酮衍生物。纳米结构催化剂易于通过过滤回收并重复使用几次，而其催化活性没有明显损失。少量的催化剂（0.005 g），较短的反应时间和绿色条件是该方法的优点。