2,7,7-trimethyl-5-oxo-4-(3,4-dichlorophenyl)-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: 2,7,7-trimethyl-5-oxo-4-(3,4-dichlorophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: 4-(3',4'-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylic acid ethyl ester；ethyl 1,4,7,8-tetrahydro-2,7,7-trimethyl-4-(3,4-dichlorophenyl)-5(6H)-oxoquinoline-3-carboxylate；Ethyl 4-(3,4-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(3,4-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₁H₂₃Cl₂NO₃
• 分子量: 408.325
• InChiKey: HIHKHRNPBLIRHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 、 3,4-二氯苯甲醛 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 0.12h， 以95%的产率得到2,7,7-trimethyl-5-oxo-4-(3,4-dichlorophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  通过二氧化锡纳米颗粒催化的四组分 Hantzsch 缩合合成聚氢喹啉衍生物

  摘要：

  二氧化锡 (SnO2) 纳米粒子有效地催化各种醛、二甲酮、乙酰乙酸乙酯和乙酸铵的不对称四组分 Hantzsch 缩合反应，以优异的产率形成聚氢喹啉衍生物。与合成这些化合物的传统方法相比，这种新方法具有多种优势，包括安全、条件温和、反应时间短、收率高和易于处理。

  DOI：

  10.1016/s1872-2067(11)60518-4

文献信息

• Four-component synthesis of polyhydroquinolines under catalyst- and solvent-free conventional heating conditions: mechanistic studies
  作者：Pipattra Mayurachayakul、Wanchai Pluempanupat、Choladda Srisuwannaket、Oraphin Chantarasriwong

  DOI：10.1039/c7ra13120h

  日期：——

  A convenient and environmentally friendly procedure for the synthesis of polyhydroquinolines via a one-pot, four component condensation of different aromatic aldehydes with dimedone, ethyl acetoacetate and ammonium acetate has been developed. Upon heating at 100 °C, the desired products were produced in good to excellent yields with short reaction times under catalyst- and solvent-free conditions.

  已经开发了一种方便且对环境友好的方法，该方法用于通过将不同芳族醛与二甲酮，乙酰乙酸乙酯和乙酸铵进行一锅，四组分缩合来合成聚氢喹啉。在100°C下加热后，在无催化剂和无溶剂条件下，以较短的反应时间以良好的产率获得了所需的产品。机理研究表明，两种可能的途径可以解释聚氢喹啉的四组分合成。出乎意料的是，第一个涉及烯胺对迈克尔中间体的亲核攻击，然后是逆醛醇型反应和六电子环环化。先前已提出的第二种方法包括将Knoevenagel中间体与烯胺进行迈克尔加成反应。
• Cu(II) Schiff Base Complex as a Highly Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation in Water
  作者：Seyed Vahdat

  DOI：10.2174/13862073113169990003

  日期：2013.11

  In the present study, Cu(II) Schiff-base complex is introduced as a highly efficient and green solid catalyst for the unsymmetrical Hantzsch condensation through a four-component coupling of various aldehydes, dimedone, ethyl acetoacetate and ammonium acetate to form polyhydroquinoline derivatives in good to excellent yields. This reaction was carried out in the presence of 1 mol% of catalysts in water at room temperature. The reusability of the catalysts was demonstrated by a five-run test. Remarkable features of this new procedure are cleaner reaction profiles, shorter reactiontimes, simple experimental and work-up procedures.

  在本研究中，Cu(II)席夫碱复合物被介绍为一种高效且绿色的固体催化剂，用于不对称Hantzsch缩合反应，通过多种醛、二甲酮、乙酰乙酸乙酯和醋酸铵的四组分偶联反应形成多氢奎啉衍生物，产率良好到优异。该反应在室温下以1 mol%的催化剂在水中进行。催化剂的重复使用性通过五轮测试得到了证明。这种新方法的显著特点是反应过程更清洁、反应时间更短、实验和后处理程序更简单。
• Synthesis of polyhydroquinoline derivatives via a four-component Hantzsch condensation catalyzed by tin dioxide nanoparticles
  作者：Seyed Mohammad VAHDAT、Fereshteh CHEKIN、Mehdi HATAMI、Maryam KHAVARPOUR、Saeed BAGHERY、Ziba ROSHAN-KOUHI

  DOI：10.1016/s1872-2067(11)60518-4

  日期：2013.4

  Tin dioxide (SnO2) nanoparticles efficiently catalyzed unsymmetrical four-component Hantzsch condensations of various aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate to form polyhydroquinoline derivatives in excellent yields. This novel method offers several advantages over the traditional method of synthesizing these compounds, including safety, mild conditions, short reaction times

  二氧化锡 (SnO2) 纳米粒子有效地催化各种醛、二甲酮、乙酰乙酸乙酯和乙酸铵的不对称四组分 Hantzsch 缩合反应，以优异的产率形成聚氢喹啉衍生物。与合成这些化合物的传统方法相比，这种新方法具有多种优势，包括安全、条件温和、反应时间短、收率高和易于处理。
• P-TSA Catalyzed Facile and Efficient Synthesis of Polyhydroquinoline Derivatives through Hantzsch Multi-Component Condensation
  作者：Sanjeeva Reddy Cherkupally、Raghu Mekala

  DOI：10.1248/cpb.56.1002

  日期：——

  A facile and efficient synthetic route to polyhydroquinolines has been developed via four-component condensation reactions of aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of p-toluenesulfonic acid (p-TSA) catalyst in ethanol at ambient temperature through Hantzsch reaction. Simple work-up procedure, environmentally friendly, inexpensive and non-toxic catalyst, shorter

  通过在环境温度下通过Hantzsch反应在乙醇中对甲苯磺酸（p-TSA）催化剂存在下，通过醛，二甲酮，乙酰乙酸乙酯和乙酸铵的四组分缩合反应，已经开发了一种简便有效的合成多氢喹啉的途径。简单的后处理程序，环保，廉价且无毒的催化剂，较短的反应时间以及优异的产品收率是该实用方法的重要特征。
• Synthesis, characterization, crystal structure and anticancer activity of tetrahydro-quinolines using silica iodide as a heterogeneous catalyst
  作者：K.B. Ramesh、B.M. Omkaramurthy、M. Srinivas

  DOI：10.1016/j.molstruc.2020.128790

  日期：2020.12

  Abstract An efficient synthesis of tetrahydroquinolines using silica iodide as heterogeneous catalyst. Ethyl acetoacetate, dimedone, ammonium acetate with suitable aromatic aldehydes in ethanol was reported. Silica iodide (SiO2–I) acts as an efficient heterogeneous catalyst to afford the products in excellent yield in short reaction duration and reusable catalyst. The synthesized 4 d and 4 h compounds

  摘要 以碘化硅为多相催化剂高效合成四氢喹啉。据报道，乙酰乙酸乙酯、二甲酮、乙酸铵与合适的芳香醛在乙醇中。碘化硅（SiO2-I）作为一种高效的多相催化剂，可以在较短的反应时间和可重复使用的催化剂中以优异的产率提供产品。合成的 4 d 和 4 h 化合物通过单晶 X 射线衍射法表征。此外，制备的喹啉衍生物对 HepG2 和 MCF-7 细胞系显示出有效的抗癌活性。进行对接研究以评估合成化合物和标准药物阿霉素与雌激素受体 (ER) 的结合亲和力。