2-(4-methoxyphenyl)-4-phenyl-1-tosyl-1H-imidazole | 1078739-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-methoxyphenyl)-4-phenyl-1-tosyl-1H-imidazole
• 英文别名: 2-(4-methoxyphenyl)-1-[(4-methylphenyl)sulfonyl]-4-phenyl-1H-imidazole；2-(4-Methoxyphenyl)-1-(4-methylphenyl)sulfonyl-4-phenylimidazole
• CAS: 1078739-28-2
• 化学式: C₂₃H₂₀N₂O₃S
• 分子量: 404.489
• InChiKey: BMUZDMQSXPCFGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 在 四(三苯基膦)钯 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 sodium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 20.5h， 生成 2-(4-methoxyphenyl)-4-phenyl-1-tosyl-1H-imidazole
  参考文献：
  名称：

  Synthesis of 2-Bromoimidazoles from Alkynes, N-Sulfonylazides, and Bromocyanides

  摘要：

  A synthetic method for Z-bromoimidazoles is developed from Rh-catalyzed cyclization of N-sulfonyl-1,2,3-triazoles with bromocyanides. Cu-catalyzed [3 + 2] cycloaddition followed by Rh-catalyzed cyclization starting from alkynes, N-sulfonylazides, and bromocyanides is also demonstrated for de novo synthesis of 2-bromoimidazoles in one pot. Moreover, this work was successfully employed to introduce diverse functional groups to the 2-position of imidazoles via cross-coupling reaction.

  DOI：

  10.1021/acs.orglett.5b00977

文献信息

• Thermal Ring Expansion of 2-Sulfonylimidoyl-1-phthalimidoaziridines into <i>N</i> -Sulfonylimidazoles
  作者：Aleksandr Stukalov、Vitalii V. Suslonov、Mikhail A. Kuznetsov

  DOI：10.1002/ejoc.201701806

  日期：2018.4.17

  Di‐, tri‐substituted, and spiro‐fused 2‐sulfonylimidoyl‐1‐phthalimidoaziridines are transformed to di‐, tri‐substituted, and condensed N‐sulfonylimidazoles upon thermolysis. This ring expansion is accompanied by an intramolecular 1,3‐sulfonyl shift.

  在热解后，二，三取代和螺旋稠合的2-磺酰亚胺基1-1-邻苯二甲酰亚胺基氮杂环丁烷转化为二，三取代和缩合的N-磺酰亚胺基咪唑。这种环的扩张伴随着分子内的1,3-磺酰基转移。
• Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles
  作者：Tony Horneff、Stepan Chuprakov、Natalia Chernyak、Vladimir Gevorgyan、Valery V. Fokin

  DOI：10.1021/ja805079v

  日期：2008.11.12

  Stable and readily available 1-sulfonyl triazoles are converted to the corresponding imidazoles in good to excellent yields via a rhodium(II)-catalyzed reaction with nitriles. Rhodium iminocarbenoids are proposed intermediates.