2,7,7-trimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-quinoline-3-carboxylic acid ethyl ester | 13337-65-0

• 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: 2,7,7-trimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-3-quinolinecarboxylate；ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-6,8-dihydroquinoline-3-carboxylate
• CAS: 13337-65-0
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: HMPNSVDJZAEYIL-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  492.0±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 1,4,7,8-tetrahydro-2,7,7-trimethyl-4-phenyl-5(6H)-oxoquinoline-3-carboxylate 在 叔丁基过氧化氢 、 sodium dithionite 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 以89%的产率得到2,7,7-trimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  A new oxidation system for the oxidation of Hantzsch-1,4-dihydropyridines and polyhydroquinoline derivatives under mild conditions

  摘要：

  已开发出一种氧化系统，通过氧化1,4-二氢吡啶和多羟基喹啉衍生物，可以高产率合成吡啶衍生物。

  DOI：

  10.1039/c5ra20977c

文献信息

• A new oxidation system for the oxidation of Hantzsch-1,4-dihydropyridines and polyhydroquinoline derivatives under mild conditions
  作者：Cui-Bing Bai、Nai-Xing Wang、Yan-Jing Wang、Xing-Wang Lan、Yalan Xing、Jia-Long Wen

  DOI：10.1039/c5ra20977c

  日期：——

  An oxidation system to synthesize pyridine derivatives has been developed by oxidation of 1,4-dihydropyridines and polyhydroquinoline derivatives in good yields.

  已开发出一种氧化系统，通过氧化1,4-二氢吡啶和多羟基喹啉衍生物，可以高产率合成吡啶衍生物。
• One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation
  作者：Tahere Akbarpoor、Ardeshir Khazaei、Jaber Yousefi Seyf、Negin Sarmasti、Maryam Mahmoudiani Gilan

  DOI：10.1007/s11164-019-04049-y

  日期：2020.2

  In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8 mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation.

  在本项研究中，通过欧洲联盟法规界定为危险废物的蛋壳被转化为一种有价值的催化剂，即纳米Fe3O4@(HSO4)2。所制备的催化剂首先通过多种技术进行了表征，包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、能量色散X射线光谱（EDX）、场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）。反滴定法证实了催化剂表面存在高密度的酸性基团，具体为每克催化剂含有8.8 mmol HSO4。通过异头氧化（ABO）合成2-氨基-3-氰基吡啶以及六氢喹啉衍生物时，考察了所制备催化剂的催化性能。高产率、短反应时间、无溶剂条件、废物利用以及结合实验设计的优化是本工作的主要优势。综合来看，这些结果表明了废物在全球范围内的财富转化潜力，并可用于有机转化过程。
• Microwave assisted combinatorial chemistry synthesis of substituted pyridines
  作者：Ian C. Cotterill、Alexander Ya. Usyatinsky、John M. Arnold、Douglas S. Clark、Jonathan S. Dordick、Peter C. Michels、Yuri L. Khmelnitsky

  DOI：10.1016/s0040-4039(97)10796-1

  日期：1998.3

  (Microwave-assisted Combinatorial Synthesis) for generating combinatorial libraries is described. The technology is applied to the high throughput, automated, one-step, parallel synthesis of diverse substituted pyridines using the Hantzsch synthesis. The advantages of microwave-assisted chemistry for combinatorial synthesis include a broad range of available chemistries, simple reaction setup and product

  描述了一种用于生成组合库的新型高效MICROCOS技术（微波辅助组合合成）。该技术已应用于使用Hantzsch合成技术的高通量，自动化，一步一步，多种取代吡啶的并行合成中。微波辅助化学用于组合合成的优点包括广泛的可用化学方法，简单的反应设置和易于自动化的产物回收，极短的反应时间以及高产物收率。
• Development of Porous Organic Polymers as Metal‐Free Photocatalysts for the Aromatization of <i>N</i>‐Heterocycles
  作者：Maarten Debruyne、Nathan Raeymackers、Henk Vrielinck、Sambhu Radhakrishnan、Eric Breynaert、Maxime Delaey、Andreas Laemont、Karen Leus、Jonas Everaert、Hannes Rijckaert、Dirk Poelman、Rino Morent、Nathalie De Geyter、Pascal Van Der Voort、Veronique Van Speybroeck、Christian V. Stevens、Thomas S. A. Heugebaert

  DOI：10.1002/cctc.202301205

  日期：2024.4.8

  Porous organic polymers (POPs), and especially covalent triazine frameworks (CTFs), are being developed as the next generation of metal‐free heterogeneous photocatalysts. However, many of the current synthetic routes to obtain these photoactive POPs require expensive monomers and rely on precious metal catalysts, thus hindering their widespread implementation. In this work, a range of POPs was synthesized from simple unfunctionalized aromatic building blocks, through Lewis acid‐catalyzed polymerization. The obtained materials were applied, for the first time, as heterogeneous photocatalysts for the aromatization of N‐heterocycles. With the use of the most active material, denoted as CTF‐Pyr, which consists of photoactive pyrene and triazine moieties, a wide range of pyridines, dihydroquinoline‐5‐ones, tetrahydroacridine‐1,8‐diones and pyrazoles were obtained in excellent yields (70–99 %). Moreover, these reactions were carried out under very mild conditions using air and at room temperature, highlighting the potential of these materials as catalysts for green transformations.

  摘要 多孔有机聚合物（POPs），尤其是共价三嗪框架（CTFs），正被开发为下一代无金属异相光催化剂。然而，目前获得这些光活性持久性有机聚合物的许多合成路线都需要昂贵的单体并依赖贵金属催化剂，因此阻碍了它们的广泛应用。在这项研究中，我们通过路易斯酸催化聚合反应，从简单的非官能化芳香族结构单元合成了一系列持久性有机污染物。所获得的材料首次被用作 N-杂环芳香化的异相光催化剂。使用活性最高的材料 CTF-Pyr（由具有光活性的芘和三嗪分子组成），可以获得多种吡啶、二氢喹啉-5-酮、四氢吖啶-1,8-二酮和吡唑，收率极高（70-99%）。此外，这些反应都是在非常温和的条件下，利用空气在室温下进行的，突出了这些材料作为绿色转化催化剂的潜力。