1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat | 126412-02-0

• 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: 1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat
• 英文别名: Methyl 2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；methyl 2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 126412-02-0
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: CGNRGBIADYYMNW-UHFFFAOYSA-N

物化性质

• 熔点：
  273-275 °C(Solv: ethanol (64-17-5))
• 沸点：
  517.0±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat 在 pyridinium hydrobromide perbromide 作用下， 以 氯仿 为溶剂， 以32%的产率得到9-(o-nitrophenyl)-6,6-dimethyl-1,8-dioxo-1,3,4,5,7,8-dodecahydrofuro<3,4-b>quinoline
  参考文献：
  名称：

  Rose, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 11, p. 1393 - 1398

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 硝苯啶杂质C 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以80%的产率得到1,4,5,6,7,8-Hexahydro-2,7,7-trimethyl-4-(2-nitrophenyl)-5-oxo-chinolin-3-methylat
  参考文献：
  名称：

  Sainani, J. B.; Shah, A. C.; Arya, V. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 6, p. 526 - 531

  摘要：

  DOI：

文献信息

• Zn/MCM-41-catalyzed unsymmetrical Hantzsch reaction and the evaluation of optical properties and anti-cancer activities of the polyhydroquinoline products
  作者：Elaheh Farajzadeh Oskuie、Sajjad Azizi、Zarrin Ghasemi、Mahtab Pirouzmand、Behnaz Nikzad Kojanag、Jafar Soleymani

  DOI：10.1007/s00706-020-02549-x

  日期：2020.2

  investigated in the presence of MCM-41-supported ZnNO3. The polyhydroquinoline products which were obtained under mild conditions and very easy workup were evaluated for anti-cancer activities against MCF-7, SK-BR-3, and HT-29 of breast and colon cancer cells. The fluorescence emission of some products was also studied and their optical parameters were reported. Graphic abstract

  摘要在MCM-41负载的ZnNO 3的存在下，研究了各种芳基醛，二甲酮和3-氨基巴豆酸甲酯的三组分Hantzsch缩合反应。评价了在温和条件下和很容易处理后获得的聚氢喹啉产品对乳腺癌和结肠癌细胞的MCF-7，SK-BR-3和HT-29的抗癌活性。还研究了一些产物的荧光发射，并报道了它们的光学参数。 图形摘要
• Sulfuric acid heterogenized on magnetic Fe₃ O₄ nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions
  作者：Lotfi Shiri、Setare Zarei、Mosstafa Kazemi、Davood Sheikh

  DOI：10.1002/aoc.3938

  日期：2018.1

  Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs‐OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco‐friendly advantages of this catalytic system. It is noteworthy

  成功地合成了固定在磁性Fe 3 O 4纳米颗粒上的硫酸（Fe 3 O 4 MNPs-OSO 3 H）作为一种新型固体酸纳米复合材料，并研究了其在一系列缩合反应中的催化活性。高催化活性，通过外部磁体与反应混合物的简单分离以及良好的可重复使用性是该催化系统的多项环保优势。值得注意的是，该催化体系适用于广泛范围的芳族醛，并且在温和的条件下以良好或优异的收率获得了所需的产物。从环境的角度来看，使用生态友好型溶剂也使该合成方案理想且引人入胜。
• PEG-Mediated Catalyst-Free Synthesis of Hantzsch 1,4-Dihydropyridines and Polyhydroquinoline Derivatives
  作者：V. Siddaiah、G. Mahaboob Basha、G. Padma Rao、U. Viplava Prasad、R. Suryachendra Rao

  DOI：10.1080/00397911.2010.528289

  日期：2012.3.1

  Abstract Hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives were synthesized in good yields by PEG-mediated, catalyst–free synthesis under solvent-free conditions. The products were directly recrystallized from hot methanol. The reaction gave excellent yields with low- as well as high-molecular-weight polyethylene glycols. GRAPHICAL ABSTRACT

  摘要 Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物在无溶剂条件下通过PEG介导的无催化剂合成以良好的收率合成。产物直接从热甲醇中重结晶。该反应对低分子量和高分子量聚乙二醇产生了极好的收率。图形概要
• One-pot multicomponent synthesis hexahydroquinoline derivatives in Triton X-100 aqueous micellar media
  作者：Mohammad Reza Poor Heravi、Shadi Mehranfar、Nemat Shabani

  DOI：10.1016/j.crci.2012.11.017

  日期：2014.2

  Résumé A facile and efficient synthesis of hexahydroquinoline derivatives (5a–o) was reported via a four-component condensation reaction of aldehydes, dimedone, methyl aceto acetate and ammonium acetate in the presence of Triton X-100 in water at room temperature. The use of just 20 mol % of Triton X-100 in water solvent is sufficient. The FT-IR, 19F NMR, 1H NMR, 13C NMR spectra and elemental analysis confirm the structure of the compounds.

  简述 在室温下，在水溶剂 Triton X-100 的存在下，通过醛、二甲基酮、乙酰乙酸甲酯和乙酸铵的四组分缩合反应，简便高效地合成了六氢喹啉衍生物 (5a-o)。在水溶剂中只需使用 20 摩尔 % 的 Triton X-100 即可。傅立叶变换红外光谱、19F NMR、1H NMR、13C NMR 光谱和元素分析证实了这些化合物的结构。
• Ahluwalia; Goyal, Bindu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 10, p. 1021 - 1025
  作者：Ahluwalia、Goyal, Bindu

  DOI：——

  日期：——