3,5-dimethyl-1-phenyl-4-(p-tolylthio)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-dimethyl-1-phenyl-4-(p-tolylthio)-1H-pyrazole
• 英文别名: 3,5-Dimethyl-4-((4-methylphenyl)thio)-1-phenyl-1H-pyrazole；3,5-dimethyl-4-(4-methylphenyl)sulfanyl-1-phenylpyrazole
• 化学式: C₁₈H₁₈N₂S
• 分子量: 294.42
• InChiKey: ZEZVWKXCZOIDLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲基-1-苯基吡唑 、 4-甲苯硫酚 在 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate 、 碘 、 氧气 作用下， 以 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 120.0h， 以82%的产率得到3,5-dimethyl-1-phenyl-4-(p-tolylthio)-1H-pyrazole
  参考文献：
  名称：

  Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin–Iodine Catalysis

  摘要：

  Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water as the only byproduct. The methodology was also extended to the sulfenylation of pyrazoles and electron-rich benzenes and afforded a series of thioethers in good yields.

  DOI：

  10.1021/acs.joc.9b02422

文献信息

• Metal- and solvent-free, iodine-catalyzed cyclocondensation and C H bond sulphenylation: A facile access to C-4 sulfenylated pyrazoles via a domino multicomponent reaction
  作者：Pengfei Sun、Daoshan Yang、Wei Wei、Xuejun Sun、Wenhui Zhang、Hui Zhang、Yu Wang、Hua Wang

  DOI：10.1016/j.tet.2017.02.046

  日期：2017.4

  We describe herein a green and efficient MCRs protocol to synthesize C-4 sulfenylated pyrazoles by iodine-catalyzed cyclocondensation and direct C-H bond sulphenylation reactions. Through this protocol, two new C-N bonds and one C-S bond are constructed simultaneously in a single step. This method provides a straightforward and sustainable way to construct valuable sulfenylated pyrazoles under metal- and solvent-free conditions. (C) 2017 Published by Elsevier Ltd.
• Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation
  作者：Jun Sun、Jiang-Kai Qiu、Yi-Long Zhu、Cheng Guo、Wen-Juan Hao、Bo Jiang、Shu-Jiang Tu

  DOI：10.1021/acs.joc.5b01280

  日期：2015.8.21

  A direct and metal-free access toward fully substituted pyrazoles and its sulphenylation has been established through an iodine-mediated three-component [3 + 2] annulation of beta-ketonitrile (or pentane-2,4-dione), arylhydrazines, and aryl sulfonyl hydrazides. The reaction allows the formation of one C-S and two C-N bonds by the multiple bond cleavage including sulfur-oxygen, sulfur-nitrogen, and carbon-oxygen bonds. The method features low-cost and readily accessible substrates, bond-forming efficiency, and broad substrate scopes as well as simple one-pot operation, which makes this strategy highly attractive.
• Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin–Iodine Catalysis
  作者：Kazumasa Tanimoto、Ryoma Ohkado、Hiroki Iida

  DOI：10.1021/acs.joc.9b02422

  日期：2019.11.15

  Two-component metal-free catalytic oxidative sulfenylation of pyrazolones with thiols has been achieved using the biomimetic flavin and iodine. The methodology is mild and eco-friendly, proceeds in the presence of air or molecular oxygen (1 atm) as the sole sacrificial reagent, and generates water as the only byproduct. The methodology was also extended to the sulfenylation of pyrazoles and electron-rich benzenes and afforded a series of thioethers in good yields.