5-[4-(methylsulfonyl)phenyl]-3-phenylisoxazole | 1350470-08-4

• 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: 5-[4-(methylsulfonyl)phenyl]-3-phenylisoxazole
• 英文别名: 5-(4-Methylsulfonylphenyl)-3-phenyl-1,2-oxazole
• CAS: 1350470-08-4
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: LEOLCQBMJPZGMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzohydroximoyl chloride 在 potassium phosphate 、 氯(2-二环己基膦基-2',4',6'-三异丙基-1,1'-联苯基)[2-(2'-氨基-1,1'-联苯)]钯(II) 、 copper(II) acetate monohydrate 、 potassium carbonate 作用下， 以 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 18.33h， 生成 5-[4-(methylsulfonyl)phenyl]-3-phenylisoxazole
  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

• Novel valdecoxib derivatives by ruthenium(<scp>ii</scp>)-promoted 1,3-dipolar cycloaddition of nitrile oxides with alkynes – synthesis and COX-2 inhibition activity
  作者：Silvia Roscales、Nicole Bechmann、Daniel Holger Weiss、Martin Köckerling、Jens Pietzsch、Torsten Kniess

  DOI：10.1039/c7md00575j

  日期：——

  Novel valdecoxib-based cyclooxygenase-2 inhibitors were synthesized in one step via 1,3-dipolar cycloaddition of nitrile oxides with a series of eleven aryl alkynes, six of them described for the first time. Application of Ru(II)-catalysis leads preferably to the formation of the 3,4-diaryl-substituted isoxazoles, while under thermal heating with base the 3,5-diaryl substitution pattern is favoured

  通过将腈与一系列十一个芳基炔烃进行1,3-偶极环加成反应，一步合成了一种新的基于valdecoxib的环氧合酶-2抑制剂，其中六个首次被描述。Ru（II）催化的应用优选导致3，4-二芳基取代的异恶唑的形成，而在与碱一起热加热下，有利于3，5-二芳基取代的模式。具有小的取代基（H和Me）的新的3,4-二芳基取代的异恶唑显示出高的COX-2抑制亲和力（IC 50= 0.042–0.073μM）和优异的选择性（COX-2 SI> 2000）。相反，3，5-二芳基取代的化合物几乎没有表现出COX活性。4-氟苯基取代基的引入导致保留了较高的COX-2亲和力，使这些化合物与可行的一步反应一起有望成为开发氟18标记的放射性示踪剂的候选物。
• 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.