2-amino-7,7-dimethyl-5-oxo-4-(4-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester

• 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-4-(4-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-amino-1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxoquinoline-3-carboxylate；Ethyl 2-amino-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate；ethyl 2-amino-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: PPDNSHTYQXNSHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以80%的产率得到2-amino-7,7-dimethyl-5-oxo-4-(4-methoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  在温和条件下制备的ClO 4-/ Zr-MCM-41纳米颗粒：用于合成多氢喹啉的新型固体酸催化剂

  摘要：

  醛，双甲酮，氰基乙酸乙酯或乙酰乙酸乙酯和乙酸铵的一锅四组分反应在perchlorated Zr的MCM-41（CLO的存在下研究了4 -纳米颗粒为二氢吡啶的合成/ Zr的MCM-41）。Zr的MCM-41的纳米颗粒有Si / Zr的的各种摩尔比采用溶胶-凝胶方法在温和的条件下合成，然后CLO 4 -制备/ Zr的MCM-41样品与不同的煅烧温度下和通过XRD，FT红外和扫描电镜技术。表征结果显示，高氯酸的存在下，在的细微结构Zr的MCM-41和催化性能试验表明，CLO 4 -Si / Zr摩尔比为25且煅烧温度为300°C的/ Zr-MCM-41具有最佳的催化活性。该催化剂可以容易地回收并且可以在活性适度降低的情况下多次重复使用。

  DOI：

  10.1007/s13738-016-0848-4

文献信息

• Sulfated polyborate as an eco-compatible solid acid catalyst for efficient and facile solvent-free synthesis of polyhydroquinolines
  作者：Dilip Aute、Akshay Kshirsagar、Bhagwat Uphade、Anil Gadhave

  DOI：10.1007/s12039-020-01850-w

  日期：2020.12

  and efficient protocol for the synthesis of polyhydroquinolines using sulfated polyborate catalyst have been developed by Hantzsch four-component condensation between aromatic aldehydes, dimedone, ammonium acetate and ethylacetoacetate or ethylcyanoacetate at 100 °C under solvent-free condition. The sulfated polyborate catalyst is characterized by FT-IR, XRD, SEM and EDAX techniques. The noticeable

  摘要 Hantzsch在无溶剂条件下于100°C下通过芳族醛，二甲酮，乙酸铵和乙酰乙酸乙酯或氰基乙酸乙酯之间的四组分缩合反应，开发了一种使用硫酸化多硼酸酯催化剂合成多氢喹啉的环保可行，绿色高效的方法。硫酸化多硼酸盐催化剂通过FT-IR，XRD，SEM和EDAX技术表征。该方法的显着特点是催化剂具有温和的布朗斯台德酸性性质，良好至优异的产品收率（85–94％），较短的反应时间（18–30分钟），无溶剂条件，操作简便且适用范围广基板数量（29个示例）。 图形摘要 这项工作涉及硫酸化的多硼酸酯催化的绿色和高效的无溶剂合成多氢喹啉。
• FSM-16-SO3H nanoparticles as a novel heterogeneous catalyst: preparation, characterization, and catalytic application in the synthesis of polyhydroquinolines
  作者：Somayeh Hashemi-Uderji、Mohammad Abdollahi-Alibeik、Reza Ranjbar-Karimi

  DOI：10.1515/mgmc-2018-0006

  日期：2018.8.28

  Abstract FSM-16-SO3H nanoparticles were prepared using a sol-gel method at room temperature. The prepared FSM-16-SO3H was used to catalyze the synthesis of polyhydroquinolines through a one-pot, four-component reaction of aldehydes, dimedone, ethyl cyanoacetate, and ammonium acetate under reflux condition in EtOH as a green solvent. To investigate the textural properties of the prepared catalyst, various

  摘要 FSM-16-SO3H 纳米粒子采用溶胶-凝胶法在室温下制备。制备的 FSM-16-SO3H 用于通过醛、二甲酮、氰基乙酸乙酯和乙酸铵在 EtOH 绿色溶剂中回流条件下的一锅四组分反应催化合成多氢喹啉。为了研究所制备催化剂的结构特性，应用了各种技术，如 X 射线衍射、傅里叶变换红外光谱、扫描电子显微镜和布鲁诺-埃米特-泰勒。高催化活性、易于操作和热稳定性是该催化剂的连续研究后可以表示的优越性能。此外，催化剂可以很容易地回收并有效地重复使用几个循环。
• An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding
  作者：Satish Kumar、Poonam Sharma、Kamal K. Kapoor、Maninder Singh Hundal

  DOI：10.1016/j.tet.2007.11.008

  日期：2008.1

  An efficient synthesis of polyhydroquinolines is achieved via a four-component reaction of aldehydes, dimedone, active methylene compounds, and ammonium acetate in one-pot under solvent-free conditions at room temperature on grinding. The present method does not involve any hazardous organic solvent or catalyst. The key advantages are the short reaction time, high yields, simple workup, and purification of products by non-chromatographic methods, i.e., by simple recrystallization from ethanol. (c) 2007 Elsevier Ltd. All rights reserved.
• ZnO-nanoparticle-promoted synthesis of polyhydroquinoline derivatives via multicomponent Hantzsch reaction
  作者：M. Z. Kassaee、Hassan Masrouri、Farnaz Movahedi

  DOI：10.1007/s00706-010-0252-1

  日期：2010.3

  Zinc oxide nanoparticles are used as an effective and reusable catalyst for one-pot, four-component couplings of aldehydes, dimedone, active methylene compounds, and ammonium acetate to produce polyhydroquinoline derivatives under solvent-free conditions at room temperature. Compared with other methods, satisfactory results are obtained with high yields, short reaction times, and simplicity in the experimental procedure. The catalyst could easily be recycled and reused four times without noticeable decrease in catalytic activity.