ethyl 2,7,7-trimethyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline3-carboxylate | 78080-70-3

• 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: ethyl 2,7,7-trimethyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline3-carboxylate
• 英文别名: Ethyl 2,7,7-trimethyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 2,7,7-trimethyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 78080-70-3
• 化学式: C₂₄H₃₁NO₆
• 分子量: 429.513
• InChiKey: NGEIFOVGVAGVAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 3-氨基巴豆酸乙酯 、 5,5-二甲基-1,3-环己二酮 以 乙醇 为溶剂， 反应 1.5h， 以62%的产率得到ethyl 2,7,7-trimethyl-5-oxo-4-(3,4,5-trimethoxyphenyl)-1,4,5,6,7,8-hexahydroquinoline3-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological activity of some derivatives of condensed 1,4-dihydropyridines

  摘要：

  DOI：

  10.1007/bf00765716

文献信息

• Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
  作者：Mehdi Zabihzadeh、Atefeh Omidi、Farhad Shirini、Hassan Tajik、Mohaddeseh Safarpoor Nikoo Langarudi

  DOI：10.1016/j.molstruc.2020.127730

  日期：2020.4

  Abstract —An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chromene, and polyhydroquinoline derivatives. The significant features of the presented method are ease of preparation and handling of the catalyst, high catalytic activity, short

  摘要 —一种经济实惠的基于 DABCO 的双阳离子离子盐 ([(DABCO)2C3H5OH]·2Cl) 用于合成亚芳基丙二腈、四氢苯并[b]吡喃、吡喃并[2,3-d]-嘧啶酮（硫酮），二氢吡喃并[3,2-c]色烯和聚氢喹啉衍生物。该方法的显着特点是催化剂易于制备和处理，催化活性高，反应时间短，无需柱色谱分离，后处理程序简单。此外，催化剂可以很容易地回收并在研究的反应中重复使用几个循环。
• 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。
• Solvent-free synthesis of polyhydroquinoline derivatives employing mesoporous vanadium ion doped titania nanoparticles as a robust heterogeneous catalyst via the Hantzsch reaction
  作者：G. B. Dharma Rao、S. Nagakalyan、G. K. Prasad

  DOI：10.1039/c6ra26664a

  日期：——

  nanoparticles (V–TiO2) were used as a reusable and robust heterogeneous catalyst for one-pot four component synthesis of polyhydroquinoline derivatives via the esteemed Hantzsch reaction using arylaldehyde, β-ketoester, dimedone and ammonium acetate at 80 °C under solvent-free conditions as a multi-component synthesis. On the other hand, the catalytic activity of V–TiO2 was compared with undoped commercial

  介孔钒离子掺杂的二氧化钛纳米粒子（V–TiO 2）被用作可重用且坚固的多相催化剂，用于通过使用芳醛，β-酮酸酯，二甲基酮和乙酸铵在80°C下进行的著名的Hantzsch反应，一锅合成四氢聚喹啉衍生物。 C在无溶剂条件下作为多组分合成。另一方面，V–TiO 2的催化活性将其与未掺杂的商业二氧化钛纳米催化剂进行了比较。该方案成功地与各种结构多样的芳基醛与β-酮酸酯，二甲酮和乙酸铵有关，从而提供了相应的聚氢喹啉衍生物。操作简便，反应时间短和令人满意的产率是该方案的关键特征。该催化剂可以容易地再循环和再利用，而没有催化活性的明显下降。
• Covalently anchored sulfamic acid on cellulose as heterogeneous solid acid catalyst for the synthesis of structurally symmetrical and unsymmetrical 1,4-dihydropyridine derivatives
  作者：Shrikrishna Karhale、Chandrakant Bhenki、Gajanan Rashinkar、Vasant Helavi

  DOI：10.1039/c7nj00685c

  日期：——

  energy dispersive X-ray (EDX), thermogravimetric (TGA) and CHNS analysis. The catalytic performance of the heterogeneous acid catalyst is evaluated in the synthesis of structurally symmetrical and unsymmetrical 1,4-dihydropyridines (1,4-DHPs). High conversion, shorter reaction time, cleaner reaction profile, environmentally benign solvent, simple experimental and work-up procedure, and reusability of the

  通过将氯磺酸共价接枝到氨基官能化纤维素（Cell–Pr-NHSO 3 H）上，已经制备了一种新型的非均相固体酸催化剂。通过FT-IR，固态CP / MAS 13 C-NMR光谱，场发射扫描电子显微镜（FE-SEM），能量色散X射线（EDX），热重（TGA）和CHNS评估催化剂的结构分析。在结构对称和不对称的1,4-二氢吡啶（1,4-DHPs）的合成中评估了多相酸催化剂的催化性能。高转化率，更短的反应时间，更清洁的反应过程，对环境无害的溶剂，简单的实验和后处理程序以及催化剂的可重复使用性是我们合成路线的显着特征。