ethyl 4-(2,4-dimethoxyphenyl)-2-methyl-5-oxo-1,4,6,7,8-pentahydroquinoline-3-carboxylate | 299451-76-6

• 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 4-(2,4-dimethoxyphenyl)-2-methyl-5-oxo-1,4,6,7,8-pentahydroquinoline-3-carboxylate
• 英文别名: Ethyl 4-(2,4-dimethoxyphenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(2,4-dimethoxyphenyl)-2-methyl-5-oxo-4,6,7,8-tetrahydro-1H-quinoline-3-carboxylate
• CAS: 299451-76-6
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: VWAGPYNNBWXXGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 1,3-环己二酮 、 2,4-二甲氧基苯甲醛 在 碳酸氢铵 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 反应 0.33h， 以93%的产率得到ethyl 4-(2,4-dimethoxyphenyl)-2-methyl-5-oxo-1,4,6,7,8-pentahydroquinoline-3-carboxylate
  参考文献：
  名称：

  5-Pyrrolidin-2-yltetrazole-Promoted One-Pot Hantzsch Polyhydroquinoline Synthesis Using NH4HCO3 as Nitrogen Source

  摘要：

  在无溶剂条件下，5-吡咯烷-2-基四氮唑存在下，通过醛、二甲基酮、活性亚甲基化合物和碳酸氢铵的四组分偶联反应，报道了一种直接、绿色的多氢喹啉衍生物合成方法。该方法具有收率高、程序环保、反应时间短和易于分离产物等优点。

  DOI：

  10.1071/ch08197

文献信息

• POLYHYDROQUINOLINE COMPOUNDS AND DIHYDROPYRIDINE COMPOUNDS FOR INHIBITING BETA-AMYLOID PRODUCTION
  申请人：Mullan Michael J.

  公开号：US20100119599A1

  公开（公告）日：2010-05-13

  Provided are methods of treating or reducing the risk of developing beta-amyloid production, beta-amyloid deposition, beta-amyloid neurotoxicity (including abnormal hyperphosphorylation of tau) and microgliosis associated with cerebral accumulation of Alzheimer's amyloid by administering therapeutically effective amounts of polyhydroquinoline and dihydropyridine compounds which decrease Abeta production in cells. Further provided are methods for diagnosing diseases associated with cerebral accumulation of Alzheimer's amyloid in animals or humans by administering diagnostically effective amounts of polyhydroquinoline and dihydropyridine compounds which decrease Abeta production in cells.
• A simple, safe, eco‐friendly, and unique synthesis of hexahydro‐quinolines employing Fe3O4‐MWCNT@MnO2 as a reusable catalyst
  作者：Adapaka Venkateswara Rao、Suresh Maddila、Sai Sonali Anantha、Alice Rinky Robert、Sreekantha B. Jonnalagadda

  DOI：10.1002/aoc.7543

  日期：2024.8

  This work aims to explore the catalytic potential of manganese oxide (MnO2) supported on (Fe3O4‐MWCNT) nano‐composite, which is composed of iron oxide and multi‐walled carbon nanotubes. The nano‐composite was synthesized using a simple impregnation technique. The catalyst material was extensively characterized using a variety of possible analytical methods, including X‐ray diffraction (XRD), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and energy dispersive X‐ray spectroscopy (EDS). Then, utilizing a multi‐component condensation protocol comprising substituted aldehydes, cyclohexadione, ethylacetoacetate, and NH4OAc, the catalytic efficacy of the Fe3O4‐MWCNT@MnO2 nano‐composite was assessed for synthesizing novel hexahydro‐quinoline analogues. The catalyst was found to be effective because of its huge specific surface area, stability, porosity, and distinctive exposed surfaces. The catalyst's surface exhibited an exceptionally active nature, as seen by the notably high turnover frequency. Herein, we present a reusable and effective catalytic method that produces outstanding product yields (93%–97%) under mild reaction conditions, using ethanol as a green solvent. Cost‐effectiveness, environmental safety, and high atom efficiency are achieved using the nano‐composite.