1-(3-fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one | 20124-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one
• 英文别名: 3-FPMP；1-(3-Fluorphenyl)-3-methylpyrazolon-5；2-(3-fluorophenyl)-5-methyl-2,4-dihydropyrazol-3-one；2-(3-fluorophenyl)-5-methyl-4H-pyrazol-3-one
• CAS: 20124-84-9
• 化学式: C₁₀H₉FN₂O
• 分子量: 192.193
• InChiKey: GCYFBNJJGQAMSW-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one 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
  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：

  乙酰乙酸乙酯 、 (3-氟苯基)肼 以 甲醇 为溶剂， 生成 1-(3-fluorophenyl)-3-methyl-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

文献信息

• Thrombopoietin mimetics
  申请人：——

  公开号：US20040019190A1

  公开（公告）日：2004-01-29

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy- 1 -azobenzene derivative.

  发明了非肽类TPO类似物。还发明了用于制备目前发明的化合物的新工艺和中间体。还发明了一种治疗血小板减少症的方法，包括给予需要的哺乳动物，包括人类，有效量的选择性羟基-1-偶氮苯衍生物。
• Catalytic System‐Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones
  作者：Feifei Fang、Shulei Hu、Chunpu Li、Qian Wang、Run Wang、Xu Han、Yu Zhou、Hong Liu

  DOI：10.1002/anie.202105857

  日期：2021.9.20

  system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N−N bond activation/[n+1] annulation cascade, a C(sp2)-H

  本文报道了一种催化系统控制的发散反应策略，通过精确的化学键活化/[ n +1] 环化级联，从简单易得的起始材料构建四种有趣的螺杂环骨架。四氮杂螺杂环和三氮杂螺杂环支架可以通过选择性 NN 键激活/[ n +1] 环化级联、C(sp 2 )-H 激活/[4+1] 环化和新型串联 C(sp 2 )-H/C(sp 3)−H 键活化/[4+1] 环化策略，以及广泛的底物、中等至优异的产率和有价值的转化。更重要的是，在这些转化中，我们首次捕捉到了不同催化体系下吡唑烷酮的 NN键活化和 C(sp 3 )-H 键活化。
• Electrochemical‐Induced C(sp ³ )−H Dehydrogenative Trimerization of Pyrazolones to Tripyrazolones
  作者：Jing Ma、Jianjing Yang、Kelu Yan、Xue Sun、Wei Wei、Laijin Tian、Jiangwei Wen

  DOI：10.1002/ejoc.202100988

  日期：2021.10.26

  The electrochemical-induced C(sp3)−H dehydrogenative trimerization of pyrazolones to tripyrazolones has been developed under metal- and chemical oxidant-free conditions. This electrochemical oxidative strategy can be easily scaled up for the synthesis of biologically tripyrazolones, which is beneficial for practical applications.

  在无金属和无化学氧化剂的条件下，电化学诱导的吡唑啉酮C(sp 3 )-H 脱氢三聚化为三吡唑啉酮。这种电化学氧化策略可以很容易地扩大用于合成生物三吡唑啉酮，这有利于实际应用。
• One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence
  作者：Hong Lu、Huan-Xin Zhang、Chang-Yin Tan、Jin-Yu Liu、Hao Wei、Peng-Fei Xu

  DOI：10.1021/acs.joc.9b01454

  日期：2019.8.16

  A sequential and general strategy has been successfully developed for the synthesis of spiropyrazolone scaffolds. This intriguing transformation of the asymmetric multicomponent catalysis process was realized with the combination of Michael addition/chlorination/nucleophilic substitution in a one-pot sequence, giving rise to a series of spiropyrazolones with fully substituted cyclopropanes and spi

  已经成功地开发了用于合成螺吡唑酮支架的顺序和通用策略。一键顺序结合迈克尔加成/氯化/亲核取代反应，实现了不对称多组分催化过程的这一引人入胜的转化，从而产生了一系列具有完全取代的环丙烷的螺并吡唑并酮和螺-二氢苯并呋喃，其中连续的立体构型中心良好产生具有优异立体选择性的化合物。
• Gold(<scp>i</scp>)- and rhodium(<scp>iii</scp>)-catalyzed formal regiodivergent C–H alkynylation of 1-arylpyrazolones
  作者：Xueli Wang、Xingwei Li、Yao Zhang、Lixin Xia

  DOI：10.1039/c8ob00585k

  日期：——

  Formal regiodivergent C–H alkynylation of 1-aryl-5-pyrazolones has been realized under the catalysis of Rh(III) and Au(I) complexes by using a hypervalent iodine reagent as the alkyne source. Mechanistic studies indicate that the regioselectivity is ascribed to not only the choice of the catalyst but also the nature of the substrate. The substrate scope and functional group compatibility have been

  通过使用高价碘试剂作为炔烃源，在Rh（III）和Au（I）配合物的催化下，实现了1-芳基-5-吡唑啉酮的形式区域发散C–H烷基化。机理研究表明，区域选择性不仅归因于催化剂的选择，还归因于底物的性质。底物范围和官能团的相容性已经过全面检查。