4-(3-(4-fluorophenyl)isoxazol-5-yl)benzonitrile | 1350470-09-5

• 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: 4-(3-(4-fluorophenyl)isoxazol-5-yl)benzonitrile
• 英文别名: 4-[3-(4-Fluorophenyl)-1,2-oxazol-5-yl]benzonitrile
• CAS: 1350470-09-5
• 化学式: C₁₆H₉FN₂O
• 分子量: 264.259
• InChiKey: GDCNEJHVXAVFJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-fluoro-N-hydroxybenzimidoyl chloride 在 氯(2-二环己基膦基-2',4′,6′-三异丙基-1,1′-联苯基)[2-(2-氨基乙基)苯基)]钯(II) 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.41h， 生成 4-(3-(4-fluorophenyl)isoxazol-5-yl)benzonitrile
  参考文献：
  名称：

  Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles

  摘要：

  The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki-Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MLDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki-Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.

  DOI：

  10.1021/jo201973t

文献信息

• Electrochemical assembly of isoxazoles <i>via</i> a four-component domino reaction
  作者：Yuanyuan Zhao、Xinyue Li、Simon L. Homölle、Bin Wang、Lutz Ackermann

  DOI：10.1039/d3sc05946d

  日期：——

  Multicomponent domino reactions via electrochemical annulations have emerged as a robust strategy for the rapid assembly of heterocyclics. Herein, an electrochemical annulation via a [1 + 2 + 1 + 1] four-component domino reaction was accomplished in a user-friendly undivided cell setup to assemble valuable five-membered isoxazole motifs. Our approach is characterized by a high level functional group

  通过电化学环化的多组分多米诺骨牌反应已成为杂环化合物快速组装的稳健策略。在此，通过[1 + 2 + 1 + 1]四组分多米诺骨牌反应在用户友好的未分割的单元设置中完成电化学成环，以组装有价值的五元异恶唑基序。我们的方法的特点是高水平的官能团耐受性和操作简单性，避免了预功能化基材的繁琐且耗时的制备。进行了详细的机制研究，包​​括同位素标记、动力学研究、循环伏安法 (CV) 分析和中间表征，为自由基途径提供了支持。
• Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles
  作者：Jonathan E. Grob、Jill Nunez、Michael A. Dechantsreiter、Lawrence G. Hamann

  DOI：10.1021/jo201973t

  日期：2011.12.16

  The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki-Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MLDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki-Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.