2-amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile

• 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-amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile
• 英文别名: 2-amino-5,6-dihydro-4-phenylbenzo[h]quinoline-3-carbonitrile；2-Amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile
• 化学式: C₂₀H₁₅N₃
• 分子量: 297.359
• InChiKey: QLRABALSHCEMPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄烯丙二腈 、 3,4-二氢-1(2H)-萘酮 在 乙酸铵 作用下， 以 邻二氯苯 为溶剂， 反应 0.07h， 以70%的产率得到2-amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile
  参考文献：
  名称：

  在无溶剂条件下微波辐射下改进 2-氨基-3-氰基吡啶的合成†

  摘要：

  开发了一种简单有效的方法，用于在没有溶剂/含有痕量溶剂的微波辐射下，在乙酸铵存在下，从亚芳基丙二腈 1 和酮 2 或 4 中快速合成 2-氨基-3-氰基吡啶 3-5：反应时间相当长与传统加热下获得的产量相比，产量降低。

  DOI：

  10.1039/a708521d

文献信息

• Improved Synthesis of 2-Amino-3-cyanopyridines in Solvent Free Conditions under Microwave Irradiation†
  作者：Satya Paul、Rajive Gupta、Andre Loupy

  DOI：10.1039/a708521d

  日期：——

  2-amino-3-cyanopyridines 3–5 from arylidenemalanonitriles 1 and ketones 2 or 4 in presence of ammonium acetate without solvent/containing traces of solvent under microwave irradiation:reaction times are considerably reduced with improved yields as compared to those obtained under classical heating.

  开发了一种简单有效的方法，用于在没有溶剂/含有痕量溶剂的微波辐射下，在乙酸铵存在下，从亚芳基丙二腈 1 和酮 2 或 4 中快速合成 2-氨基-3-氰基吡啶 3-5：反应时间相当长与传统加热下获得的产量相比，产量降低。
• An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents
  作者：Hassan Faidallah、Khalid Al-Shaikh、Tariq Sobahi、Khalid Khan、Abdullah Asiri

  DOI：10.3390/molecules181215704

  日期：——

  An efficient and novel method for the synthesis in moderate to good yield (72%–84%) of a series of 3-amino-1-substituted-9,10-dihydrophenanthrene-2,4-dicarbonitriles 1–5 via one-pot multi-component reactions of aldehydes, malononitrile, 1-tetralone and ammonium acetate has been delineated. Cyclocondensation attempts of aminocyanophenanthrene derivatives 1, 2, 4 and 5 with acetic anhydride in the presence of conc. H2SO4 failed and instead the diacetylamino derivatives 10–13 were obtained. All prepared compounds were structurally elucidated by various spectroscopic methods and X-ray crystallography. N,N-diacetylamino-derivatives of phenanthrene have shown good antimicrobial activity.

  一种高效且新颖的方法被描述，用于通过一锅多组分反应合成一系列3-氨基-1-取代-9,10-二氢菲-2,4-二腈（1-5），产率中等到良好（72%-84%），反应物包括醛、苹果酸腈、1-四氢萘酮和醋酸铵。对氨基氰基菲衍生物1、2、4和5与醋酸酐在浓硫酸存在下进行环缩合的尝试未能成功，而是获得了二乙酰氨基衍生物10-13。所有合成的化合物通过各种光谱方法和X射线晶体学进行结构阐明。N,N-二乙酰氨基-菲衍生物显示出良好的抗 microbial 活性。
• Cyclohexane-Fused Pyridine Derivatives with Photophysical Properties: Synthesis by “Three-Component” Domino Reaction and Structural Optimization by DFT Calculations
  作者：Cheng Guo、Jianqiang Wang、Ziping Li、Xinzhi Wang、Yixin Zhou

  DOI：10.3987/com-14-13104

  日期：——

  An environment-friendly and highly efficient method for the preparation of 2-amino-4-phenyl-3-cyano-5,6-dihydrobenzo[h]quinoline derivatives was successfully developed via arylaldehyde, 3,4-dihydro-1(2H)-naphthalenone, malononitrile, ammonium acetate in ethanol by "three-component" domino reaction under microwave irradiation. The reaction conditions were optimized by changing microwave power, temperature and time. Their structures were characterized by ESI-MS, H-1-NMR, C-13-NMR, and IR. Their photophysical properties were detected by UV-Vis and fluorescent spectra. The results of density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculations were applied to simulate spectra of the compounds, which show excellent agreement with observed spectra and provide reasonable explanation on the structures, the molecular frontier orbital, and the electronic absorption spectra.
• Divergent Syntheses of 2-Aminonicotinonitriles and Pyrazolines by Copper-Catalyzed Cyclization of Oxime Ester
  作者：Qifan Wu、Yan Zhang、Sunliang Cui

  DOI：10.1021/ol500094w

  日期：2014.3.7

  Copper-catalyzed cyclization of an oxime ester toward divergent heterocycle synthesis is reported. Oxime ester serves as an enamine precursor to cyclize with malononitrile and aldehydes for access to 2-aminonicotinonitriles in a one-pot reaction, while cyclizing with N-sulfonylimines leads to synthesis of pyrazolines.
• Synthesis, Antiproliferative, and Antiangiogenic Activities of Benzochromene and Benzoquinoline Derivatives on Prostate Cancer in vitro
  作者：Gricelda Mata、Juan Rodrigues、Neira Gamboa、Katiuska Charris、Gricela Lobo、Melina Monasterios、Milagros Avendano、Michael Lein、Klaus Jung、Claudia Abramjuk、Bianca Nitzsche、Michael Hopfner、Jaime Charris

  DOI：10.2174/1570180814666161118163844

  日期：2017.2.23

  cause of death from cancer in men. The aims of this paper are shown the development of new, rapid, and clean synthetic routes toward focused libraries of such compounds is therefore of great importance to both medicinal and synthetic chemists. Methods: The preparation of benzochromene and benzoquinoline derivatives using the Michael addition between benzylidenemalononitrile derivatives and the 1-tetralones

  背景：前列腺癌是男性第二大最常被诊断出的恶性肿瘤，被认为是男性死于癌症的第五大主要原因。本文的目的表明，针对此类化合物的聚焦库的新的，快速的，干净的合成路线的开发因此对医学和合成化学家均至关重要。 方法：据报道，在催化量的哌啶或乙酸铵存在下，分别在苄基亚甲基丙二腈衍生物和1-四氢萘酮之间使用迈克尔加成反应，制得苯并二氢萘和苯并喹啉衍生物。体外研究其对人前列腺癌细胞PC-3和LNCaP的活性。 结果：在总共56种化合物中，有12种具有细胞毒性，抑制了PC-3细胞的活力，三种活性最高的化合物对LNCaP和MatLyLu细胞也具有细胞毒性。重要的一点是，与非癌细胞（HK-2和BPH-1）相比，这三种化合物对癌细胞的毒性要大得多。 结论：三种化合物被证明是最有效的，在不同的人类和非人类前列腺癌细胞系中均显示出细胞毒性作用。该结构的抗肿瘤活性的机制似乎与抑制MMP-9有关。