4-(3-hydroxy-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester | 312724-07-5

• 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: 4-(3-hydroxy-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: 4-(3'-hydroxy-4'-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylic acid ethyl ester；ethyl-4-(3-hydroxy-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；Ethyl 4-(3-hydroxy-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 312724-07-5
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: HZHIEBKMBNOTCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异香兰素 、 乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.3h， 以85%的产率得到4-(3-hydroxy-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  碘化硅作为多相催化剂的四氢喹啉的合成、表征、晶体结构和抗癌活性

  摘要：

  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。

  DOI：

  10.1016/j.molstruc.2020.128790

文献信息

• Facile and efficient protocols for C–C and C–N bond formation reactions using a superparamagnetic palladium complex as reusable catalyst
  作者：Mohammad Ali Karimi Zarchi、Seyed Shahab Addin Darbandizadeh Mohammad Abadi

  DOI：10.1007/s11164-019-03754-y

  日期：2019.5

  Abstract Facile and efficient protocols for some multicomponent coupling reactions such as the Suzuki reaction and synthesis of polyhydroquinoline and 2,3-dihydroquinazoline-4-(1H)-one derivatives using a superparamagnetic palladium complex as catalyst have been developed. Graphical abstract

  摘要 已经开发了一些有效的协议，用于一些多组分偶联反应，例如铃木反应以及使用超顺磁性钯配合物作为催化剂合成多氢喹啉和2,3-二氢喹唑啉-4-（1 H）-one衍生物。 图形概要
• Magnetically recyclable magnetite–ceria (Nanocat-Fe-Ce) nanocatalyst – applications in multicomponent reactions under benign conditions
  作者：Manoj B. Gawande、Vasco D. B. Bonifácio、Rajender S. Varma、Isabel D. Nogueira、Nenad Bundaleski、C. Amjad A. Ghumman、Orlando M. N. D. Teodoro、Paula S. Branco

  DOI：10.1039/c3gc40375k

  日期：——

  explored for the synthesis of dihydropyridines under benign conditions; a greener protocol is described that provides a simple and efficient method for the synthesis of functionalized 1,4-dihydropyridines using a recyclable nanocatalyst. Notably, 5.22 mol% of the catalyst is sufficient to catalyze the multicomponent reaction in ethanolic medium at room temperature. Importantly, the catalyst could be easily

  通过简单的浸渍方法成功地制备了一种新型的磁铁矿纳米颗粒负载的二氧化铈催化剂（Nanocat-Fe-Ce），并通过XRD，SIMS，FEG-SEM-EDS和TEM对其进行了表征。通过X射线光电子能谱证实了Nanocat-Fe-Ce的确切性质，并注意到CeO 2纳米粒子负载在磁铁矿上，具有二次离子质谱法的证据。探索了在良性条件下纳米催化剂对二氢吡啶合成的催化活性。描述了更绿色的方案，该方案提供了使用可循环利用的纳米催化剂合成功能化的1,4-二氢吡啶的简单有效的方法。值得注意的是，5.22mol％的催化剂足以在室温下在乙醇介质中催化多组分反应。重要的是，通过使用外部磁体可以容易地将催化剂从反应混合物中分离出来并循环几次而不会损失活性。
• A green approach for the multicomponent synthesis of polyhydroquinolines and 6-unsubstituted dihydropyrimidinones using novel highly proficient acidic ionic liquid [CEMIM][MSA] as a reusable catalyst
  作者：Priyanka Patil、Suresh Kadam、Dayanand Patil、Paresh More

  DOI：10.1016/j.catcom.2022.106500

  日期：2022.10

  Carboxylic acid functionalized imidazolium based novel acidic ionic liquid [CEMIM][MSA] was synthesized using economically feasible raw materials under very mild condition. The cost effective and sustainable synthesis of polyhydroquinoline and 6-unsustituted dihydropyrimidinone derivatives in green media was first time carried out very effectively using [CEMIM][MSA] catalyst. Acidic ionic liquid catalyst

  采用经济可行的原料，在非常温和的条件下合成了羧酸官能化咪唑基新型酸性离子液体[CEMIM][MSA]。首次使用 [CEMIM][MSA] 催化剂非常有效地在绿色介质中进行了具有成本效益且可持续的多氢喹啉和 6-未取代的二氢嘧啶酮衍生物合成。具有羧酸基团的酸性离子液体催化剂[CEMIM][MSA]易于分离并重复使用多达五个循环，而其催化活性和稳定性没有太大损失。引入的催化剂在水性介质中表现出更好的催化性能，可以在更短的时间内以优异的收率获得所述化合物。
• Dihydropyridines as potential α-amylase and α-glucosidase inhibitors: Synthesis, in vitro and in silico studies
  作者：Hina Yousuf、Shahbaz Shamim、Khalid Mohammed Khan、Sridevi Chigurupati、Kanwal、Shehryar Hameed、Muhammad Naseem Khan、Muhammad Taha、Minhajul Arfeen

  DOI：10.1016/j.bioorg.2020.103581

  日期：2020.3

  Dihydropyridine derivatives 1-31 were synthesized via one-pot solvent free condition and screened for in vitro against alpha-amylase and alpha-glucosidase enzyme. The synthetic derivatives 1-31 showed good alpha-amylase inhibition in the range of IC50 = 2.21 +/- 0.06-9.97 +/- 0.08 mu M, as compared to the standard drug acarbose (IC50 = 2.01 +/- 0.1 mu M) and alpha-glucosidase inhibition in the range of IC50 = 2.31 +/- 0.09-9.9 +/- 0.1 mu M as compared to standard acarbose (IC50 = 2.07 +/- 0.1 mu M), respectively. To determine the mode of binding interactions of synthetic molecules with active sites of enzyme, molecular docking studies were also performed. Different spectroscopic techniques such as H-1, C-13 NMR, EI-MS, and HREI-MS were used to characterize all the synthetic compounds.