5-甲基-2-(3-三氟甲基-苯基)-2,4-二氢-吡唑-3-酮 | 321-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲基-2-(3-三氟甲基-苯基)-2,4-二氢-吡唑-3-酮
• 英文名称: 5-methyl-2-[3-(trifluoromethyl)phenyl]-2,4-dihydropyrazol-3-one
• 英文别名: 1-(3-trifluoromethylphenyl)-3-methyl-2-pyrazolin-5-one；1-[3-(Trifluoromethyl)phenyl]-3-methyl-2-pyrazolin-5-one；3-methyl-1-(3-trifluoromethylphenyl)-3-pyrazolin-5-one；1-(3-Trifluormethylphenyl)-3-methylpyrazolon-5；5-Methyl-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-pyrazol-3-one；5-methyl-2-[3-(trifluoromethyl)phenyl]-4H-pyrazol-3-one
• CAS: 321-05-1
• 化学式: C₁₁H₉F₃N₂O
• mdl: MFCD00443909
• 分子量: 242.2
• InChiKey: FLRFRVFQDVMRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(3-三氟甲基-苯基)-2,4-二氢-吡唑-3-酮 在 哌啶 、 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 、 正丁醇 为溶剂， 反应 3.5h， 生成 3-methyl-4-((1-(oxiran-2-ylmethyl)-1H-indol-3-yl)methylene)-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5(4H)-one
  参考文献：
  名称：

  The discovery of indole derivatives as novel hepatitis C virus inhibitors

  摘要：

  In this study, a library of in-house small molecule was screened using a HCV cell-based assay and a compound (1) containing an N-protected indole scaffold (NINS) was identified as a novel anti-HCV inhibitor. Through structure activity relationship (SAR) study, it was observed that the racemic inhibitor (10m) displayed good anti-HCV activity (EC50 = 1.02 +/- 0.10 mu M) with the excellent selectivity index (SI = 45.56). Interestingly, R-enantiomer ((R)-10m) showed better anti-HCV activity and lower cytotoxicity than S-enantiomer ((S)-10m). (R)-10m gave the best anti-HCV potency (EC50 = 0.72 +/- 0.09 mu M) with the highest selectivity index (SI > 69.44). In addition, the mechanism of action study of NINS derivatives demonstrated that NINS derivatives interfere with the early step (viral entry) of the HCV life cycle. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.062
• 作为产物：
  描述：

  双乙烯酮 生成 5-甲基-2-(3-三氟甲基-苯基)-2,4-二氢-吡唑-3-酮
  参考文献：
  名称：

  BERTHOLD, R.

  摘要：

  DOI：

文献信息

• HETEROCYCLIC COMPOUND
  申请人：Kasai Shizuo

  公开号：US20110251187A1

  公开（公告）日：2011-10-13

  The present invention relates to a compound represented by wherein each symbol is as defined in the specification, a salt thereof and the like.

  本发明涉及一种化合物，其表示为其中每个符号如规范中定义的那样，以及其盐等。
• Regioselectivity Switch in Palladium‐Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross‐Coupling
  作者：Long Li、Pengfei Luo、Yuhua Deng、Zhihui Shao

  DOI：10.1002/anie.201901511

  日期：2019.3.26

  The first Pd‐catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross‐coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds

  首次成功开发了Pd催化的不对称烯丙基[4 + 1]环加成反应。另外，调整Pd催化剂可将反应性转向前所未有的[4 + 3]环加成/交叉偶联。配体在控制反应路径中起着至关重要的作用，可以高度选择性地从相同的底物中获得不同的产物。对获得的化合物的生物学评估导致发现新的抗肿瘤靶标。提出了一种可能的机理，暗示了两个有趣的催化循环，用于与钯-丁二烯基进行环加成反应。这项研究还证明了烯丙酸酯作为1,4-双亲电子试剂和C 4合成子参与环加成反应的潜力和实用性。
• Iodine‐Catalyzed Construction of Dihydrooxepines via 3‐Methyl‐5‐Pyrazolones C−H Oxidation/Functionalization of Quinolines Cascade
  作者：Rong Zhang、Jun Wang、Weiwei Jin、Yonghong Zhang、Bin Wang、Yu Xia、Chenjiang Liu

  DOI：10.1002/ejoc.202100541

  日期：2021.7.22

  The iodine-catalyzed catalytic formal [3+3+1] annulation for the construction of a seven-membered O-heteocycle with quinoline is developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and

  开发了碘催化的催化形式 [3+3+1] 环化，用于构建带有喹啉的七元 O-杂环。该策略涉及通过正式的三组分串联反应获得具有广泛底物范围的七元二氢氧杂环庚烷。目标产物的进一步衍生得到了三氧杂环骨架，形成了天然产物和药物分子的基本核心，广泛的底物范围显示了一种优雅的合成方法。
• O‐Acylation of 3‐Methylpyrazol‐5‐ones with Acylisothiocyanates
  作者：Mykhaylo V. Vovk、Andrij V. Bol'but、Pavlo S. Lebed'

  DOI：10.1081/scc-120030702

  日期：2004.12.31

  Abstract 3‐Methylpyrazol‐5‐ones 1 react by the O‐acylation pattern with acylisothiocyanates 2 in the solvent mixture ethanol–dioxane in the presence of the equimolar amount of potassium hydroxide to produce 5‐acyloxy‐3‐methyl‐1H‐pyrazoles 3.

  摘要 在等摩尔量的氢氧化钾存在下，3-甲基吡唑-5-酮 1 通过 O-酰化模式与酰基异硫氰酸酯 2 在溶剂混合物乙醇-二恶烷中反应，生成 5-酰氧基-3-甲基-1H-吡唑 3 .
• Synthesis of 1,3-Dioxepine-Fused (Tricyclic) Bispyrazoles Involved with Pyrazolone Derivatives and Dichloromethane
  作者：Zongqiang Song、Kai Zhu、Hongqiang Jiang、Hengfa Gong、Zenghui Ye、Fengzhi Zhang

  DOI：10.1021/acs.joc.1c03121

  日期：2022.3.18

  3-dioxepine-fused (tricyclic) bispyrazoles is described. It involves a Cs2CO3-mediated O-alkylation of readily available pyrazolone derivatives with dichloromethane as the methylene source followed by PhI(OAc)2-mediated intramolecular oxidative biheteroaryl coupling under mild conditions. This scalable protocol was applied for the preparation of valuable and novel 1,3-dioxepine-fused (tricyclic) bispyrazoles

  描述了一种简单而新颖的合成新型 1,3-二氧杂环庚烷（三环）双吡唑的方法。它涉及以二氯甲烷为亚甲基源的容易获得的吡唑啉酮衍生物的 Cs 2 CO 3介导的O烷基化，然后在温和条件下进行 PhI(OAc) 2介导的分子内氧化二杂芳基偶联。这种可扩展的方案用于制备有价值的新型 1,3-二氧杂环庚烷（三环）双吡唑，可在药物或材料化学中找到应用。