2-(3-(trifluoromethyl)phenyl)phthalazin-1(2H)-one | 380191-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-(trifluoromethyl)phenyl)phthalazin-1(2H)-one
• 英文别名: 2-[3-(trifluoromethyl)phenyl]phthalazin-1-one
• CAS: 380191-68-4
• 化学式: C₁₅H₉F₃N₂O
• 分子量: 290.244
• InChiKey: SGZCKRZBJJRUSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 2-(3-(trifluoromethyl)phenyl)phthalazin-1(2H)-one 在 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-金刚烷甲酸 、 三甲基乙酸 作用下， 以25 %的产率得到2-(2-(1-oxophthalazin-2(1H)-yl)-6-(trifluoromethyl)phenyl)acetaldehyde
  参考文献：
  名称：

  碳酸亚乙烯酯作为潜在甲酰甲基替代物：钌 (II) 催化获取芳基乙醛、芳基乙酸酯和乙缩醛的便利性

  摘要：

  在此，我们报道了一种Ru(II)催化添加剂控制的二氮杂萘酮的直接甲酰甲基化和顺序脱氢酯化，以使用碳酸亚乙烯酯作为C2合成子来获得芳基乙醛、芳基乙酸酯和缩醛。使用各种对照实验并通过质谱法确认可能的中间体来阐明反应机理。

  DOI：

  10.1002/ejoc.202300847
• 作为产物：
  描述：

  3-三氟甲基苯肼 、 邻羧基苯甲醛 以 1,4-二氧六环 为溶剂， 生成 2-(3-(trifluoromethyl)phenyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  碳酸亚乙烯酯作为潜在甲酰甲基替代物：钌 (II) 催化获取芳基乙醛、芳基乙酸酯和乙缩醛的便利性

  摘要：

  在此，我们报道了一种Ru(II)催化添加剂控制的二氮杂萘酮的直接甲酰甲基化和顺序脱氢酯化，以使用碳酸亚乙烯酯作为C2合成子来获得芳基乙醛、芳基乙酸酯和缩醛。使用各种对照实验并通过质谱法确认可能的中间体来阐明反应机理。

  DOI：

  10.1002/ejoc.202300847

文献信息

• Theoretical and experimental analysis of the antioxidant features of diarylhydrazones
  作者：Swarada Peerannawar、William Horton、Anne Kokel、Fanni Török、Marianna Török、Béla Török

  DOI：10.1007/s11224-016-0867-x

  日期：2017.4

  Structural and energetic features of a series of 15 diarylhydrazone derivatives were studied via density functional theory (DFT) in order to identify the key features that most likely contribute to their antioxidant effect. Theoretical calculations were carried out at the B3LYP/6-31G(d,p) level. The calculated physicochemical parameters included the ionization potential, N-H dissociation enthalpy, proton affinity, HOMO/LUMO energies, and the band gaps of the most stable conformation of the compounds. To assess the contribution of these factors to the in vitro activity, the compounds were synthesized and their antioxidant activity was also determined in three commonly used assays. The hydrazones were evaluated for their radical scavenging against the 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS), and peroxyl (ORAC assay) radicals. The experimental radical scavenging data of the compounds have been then plotted against the physicochemical characteristics and based on the obtained fits conclusions have been drawn regarding the relative importance of the respective factors.

  通过密度泛函理论（DFT）研究了一组15种二芳基酰肼衍生物的结构和能量特征，以确定最可能对其抗氧化效果产生贡献的关键特征。理论计算采用了B3LYP/6-31G(d,p)级别。计算的物化参数包括电离势、N-H解离焓、质子亲和力、最高占据分子轨道/最低未占据分子轨道能量以及化合物最稳定构象的能隙。为了评估这些因素对体外活性的贡献，合成了这些化合物，并在三种常用试验中测定了它们的抗氧化活性。这些酰肼类化合物在自由基清除方面进行了评估，分别针对2,2-二苯基-1-苦基肼（DPPH）、2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）和过氧自由基（ORAC试验）。然后，将化合物的实验自由基清除数据与物化特性相对比，并根据所得拟合结果得出了关于各因素相对重要性的结论。
• Diaryl Hydrazones as Multifunctional Inhibitors of Amyloid Self-Assembly
  作者：Béla Török、Abha Sood、Seema Bag、Rekha Tulsan、Sanjukta Ghosh、Dmitry Borkin、Arleen R. Kennedy、Michelle Melanson、Richard Madden、Weihong Zhou、Harry LeVine、Marianna Török

  DOI：10.1021/bi3012059

  日期：2013.2.19

  The design and application of an effective, new class of multifunctional small molecule inhibitors of amyloid self-assembly are described. Several compounds based on the diaryl hydrazone scaffold were designed. Forty-four substituted derivatives of this core structure were synthesized using a variety of benzaldehydes and phenylhydrazines and characterized. The inhibitor candidates were evaluated in multiple assays, including the inhibition of amyloid beta (A beta) fibrillogenesis and oligomer formation and the reverse processes, the disassembly of preformed fibrils and oligomers. Because the structure of the hydrazone-based inhibitors mimics the redox features of the antioxidant resveratrol, the radical scavenging effect of the compounds was evaluated by colorimetric assays against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals. The hydrazone scaffold was active in all of the different assays. The structure-activity relationship revealed that the substituents on the aromatic rings had a considerable effect on the overall activity of the compounds. The inhibitors showed strong activity in fibrillogenesis inhibition and disassembly, and even greater potency in the inhibition of oligomer formation and oligomer disassembly. Supporting the quantitative fluorometric and colorimetric assays, size exclusion chromatographic studies indicated that the best compounds practically eliminated or substantially inhibited the formation of soluble, aggregated A beta species, as well. Atomic force microscopy was also applied to monitor the morphology of A beta deposits. The compounds also possessed the predicted antioxidant properties; approximately 30% of the synthesized compounds showed a radical scavenging effect equal to or better than that of resveratrol or ascorbic acid.
• Vinylene Carbonate as Latent Formylmethyl Surrogate: The Expediency of Ruthenium(II) Catalysis in Accessing Arylacetaldehydes, Arylacetates and Acetals
  作者：Dolly David Thalakottukara、Thirumanavelan Gandhi

  DOI：10.1002/ejoc.202300847

  日期：2024.2.5

  Herein, we report a Ru(II)-catalyzed additive controlled direct formylmethylation and sequential dehydrogenative esterification of phthalazinones to access arylacetaldehydes, arylacetates, and acetals using vinylene carbonate as a C2 synthon. The reaction mechanism is elucidated using various control experiments and confirmation of possible intermediates by mass spectrometry.

  在此，我们报道了一种Ru(II)催化添加剂控制的二氮杂萘酮的直接甲酰甲基化和顺序脱氢酯化，以使用碳酸亚乙烯酯作为C2合成子来获得芳基乙醛、芳基乙酸酯和缩醛。使用各种对照实验并通过质谱法确认可能的中间体来阐明反应机理。