1-methyl-5-(phenylsulfanyl)-1H-pyrazole | 1174231-61-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methyl-5-(phenylsulfanyl)-1H-pyrazole
• 英文别名: 1-methyl-5-(phenylthio)-1H-pyrazole；1-Methyl-5-phenylsulfanylpyrazole；1-methyl-5-phenylsulfanylpyrazole
• CAS: 1174231-61-8
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: AXIGFHKLUJIGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-5-(phenylsulfanyl)-1H-pyrazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到1-methyl-5-(phenylsulfinyl)-1H-pyrazole
  参考文献：
  名称：

  Nucleophilic ortho-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence

  摘要：

  Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coupling. The strategy has been adapted to allow regiospecific propargylation of the heterocyclic substrates.

  DOI：

  10.1021/ol401786d
• 作为产物：
  描述：

  1-甲基吡唑 、 S-苯基硫代苯基砜 在 2,2,6,6-tetramethyl-piperidyl-MgCl*LiCl 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到1-methyl-5-(phenylsulfanyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Fully Substituted Pyrazoles via Regio- and Chemoselective Metalations

  摘要：

  The full functionalization of the pyrazole ring was achieved by successive regioselective metalations using TMPMgCl center dot LiCl and TMP2Mg center dot 2LiCl. Trapping with various electrophiles led to trisubstituted pyrazoles. An application to the synthesis of the acaricide Tebufenpyrad is reported.

  DOI：

  10.1021/ol901208d

文献信息

• Synthesis of Fully Substituted Pyrazoles via Regio- and Chemoselective Metalations
  作者：Christina Despotopoulou、Lydia Klier、Paul Knochel

  DOI：10.1021/ol901208d

  日期：2009.8.6

  The full functionalization of the pyrazole ring was achieved by successive regioselective metalations using TMPMgCl center dot LiCl and TMP2Mg center dot 2LiCl. Trapping with various electrophiles led to trisubstituted pyrazoles. An application to the synthesis of the acaricide Tebufenpyrad is reported.
• Nucleophilic <i>ortho</i>-Allylation of Pyrroles and Pyrazoles: An Accelerated Pummerer/Thio-Claisen Rearrangement Sequence
  作者：Andrew J. Eberhart、Claudio Cicoira、David J. Procter

  DOI：10.1021/ol401786d

  日期：2013.8.2

  Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coupling. The strategy has been adapted to allow regiospecific propargylation of the heterocyclic substrates.