1-(3-Fluorphenyl)-2,3-dimethyl-pyrazolon | 6286-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-Fluorphenyl)-2,3-dimethyl-pyrazolon
• 英文别名: 2-(3-fluoro-phenyl)-1,5-dimethyl-1,2-dihydro-pyrazol-3-one；2-(3-Fluorophenyl)-1,5-dimethyl-1,2-dihydro-3h-pyrazol-3-one；2-(3-fluorophenyl)-1,5-dimethylpyrazol-3-one
• CAS: 6286-80-2
• 化学式: C₁₁H₁₁FN₂O
• 分子量: 206.22
• InChiKey: GFRLRQFXBGYRAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.7±42.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Fluorphenyl)-2,3-dimethyl-pyrazolon 、 1-[(三异丙基硅烷基)乙炔基]-1,2-苯碘酰-3(1H)-酮 在 吡啶 、 gold(I) chloride 作用下， 以 二丁醚 为溶剂， 反应 14.0h， 以70%的产率得到2-(3-fluorophenyl)-1,5-dimethyl-4-((triisopropylsilyl)ethynyl)-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  金（i）和铑（iii）催化的1-芳基吡唑酮的正式区域发散性C–H炔基化†

  摘要：

  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。

  DOI：

  10.1039/c8ob00585k
• 作为产物：
  描述：

  (3-氟苯基)肼 在 calcium oxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(3-Fluorphenyl)-2,3-dimethyl-pyrazolon
  参考文献：
  名称：

  Pyrazolone methylamino piperidine derivatives as novel CCR3 antagonists

  摘要：

  The discovery and optimization of a novel class of potent CCR3 antagonists is described. Details of synthesis and SAR are given together with some ADME properties of selected compounds. An optimal balance between activities, physicochemical properties, and in vitro metabolic stability was reached by the proper choice of substituents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.035

文献信息

• Ruthenium(II)-Catalyzed Oxidative Double C–H Activation and Annulation Reaction: Synthesis of Indolo[2,1-<i>a</i>]isoquinolines
  作者：Somadrita Borthakur、Bipul Sarma、Sanjib Gogoi

  DOI：10.1021/acs.orglett.9b02871

  日期：2019.10.4

  The first metal-catalyzed double aryl C(sp2)-H bond activation of antipyrine and alkyne annulation reaction is reported. This Ru(II)-catalyzed reaction was accomplished in the presence of 20 mol % phosphine ligand tricyclohexylphosphine tetrafluoroborate to afford indolo[2,1-a]isoquinolines that are very important compounds because of their bioactivity and interesting optical properties.

  报告了安替比林和炔烃环化反应的第一个金属催化的双芳基C（sp2）-H键活化。该Ru（II）催化的反应在20mol％膦配体三环己基膦四氟硼酸酯的存在下完成，从而得到吲哚[2，1-a]异喹啉，由于它们的生物活性和令人感兴趣的光学性质，它们是非常重要的化合物。
• Pd(<scp>ii</scp>)-Catalyzed regioselective functionalization of antipyrines: synthesis of pyrazolono-maleimides and pyrazolono-quinones
  作者：Priya Sonowal、Pratiksha Bhorali、Sabera Sultana、Sanjib Gogoi

  DOI：10.1039/d1ob00819f

  日期：——

  A Pd(II)-catalyzed direct functionalization reaction of the 4Csp2–H bond of antipyrine derivatives is reported. This metal-catalyzed reaction of antipyrines with maleimides provided an easy and efficient access to biologically important pyrazolonomaleimides. This catalytic system is also applicable for C-4 functionalization of the antipyrine ring with quinone derivatives.

  报道了安替比林衍生物的 4Csp 2 -H 键的Pd( II ) 催化的直接官能化反应。安替比林与马来酰亚胺的这种金属催化反应提供了一种简单而有效的获得生物学上重要的吡唑啉酮马来酰亚胺的途径。该催化体系也适用于用醌衍生物对安替比林环进行 C-4 官能化。
• Pyrazolone methylamino piperidine derivatives as novel CCR3 antagonists
  作者：Cécile Pégurier、Philippe Collart、Pierre Danhaive、Sabine Defays、Michel Gillard、Frédéric Gilson、Thierry Kogej、Patrick Pasau、Nathalie Van Houtvin、Marc Van Thuyne、BerendJan van Keulen

  DOI：10.1016/j.bmcl.2007.05.035

  日期：2007.8

  The discovery and optimization of a novel class of potent CCR3 antagonists is described. Details of synthesis and SAR are given together with some ADME properties of selected compounds. An optimal balance between activities, physicochemical properties, and in vitro metabolic stability was reached by the proper choice of substituents. (c) 2007 Elsevier Ltd. All rights reserved.
• 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。