4-(4′-bromophenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-thiazole | 1597438-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4′-bromophenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-thiazole
• 英文别名: [4-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]phenyl]-pentafluoro-lambda6-sulfane；[4-[4-(4-bromophenyl)-1,3-thiazol-2-yl]phenyl]-pentafluoro-λ6-sulfane
• CAS: 1597438-19-1
• 化学式: C₁₅H₉BrF₅NS₂
• 分子量: 442.271
• InChiKey: SSHQQPSIZLZPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 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：
  42.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-pentafluorosulfanylbenzothioamide 、 2,4'-二溴苯乙酮 以 乙醇 为溶剂， 反应 2.0h， 以99%的产率得到4-(4′-bromophenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-thiazole
  参考文献：
  名称：

  2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅Groups: A Synthetic and Structural Study

  摘要：

  A series of new 2,4-diaryl-1,3-chalcogen azoles having pentafluorosulfanyl SF5 functional groups has been prepared by means of the two-component cyclization of the selenoamide or thioamide with alpha-bromoketones. The selenoamides or thioamides were obtained from the reaction of Woollins' reagent or Lawesson's reagent with 4-pentafluorosulfanylbenzonitrile, followed by hydrolysis with water. All new compounds were characterised by H-1, C-13, Se-77, F-19 NMR spectroscopy and accurate mass measurement. X-ray crystal structure analysis of the selenoamide, thioamide and 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles reveal that the selenoamide and thioamide have very similar structural features along with similar intermolecular interactions such as the pi-pi stacking and the weak N-H center dot center dot center dot E (E = S or Se) hydrogen bonding. The 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles show the newly formed five-membered N(1)-C(2)-E(3)-C(4)-C(5) ring is either perfectly planar (and coplanar with two peripheral aryl ring planes) or near-planar. The pi-pi intermolecular interactions and the weak C-H center dot center dot center dot pi and C-H center dot center dot center dot X (X = Br, F, O) hydrogen bonding are discussed in the cases of 2,4-diarylpentafluorosulfanyl-1,3-chalcogen azoles.

  DOI：

  10.1021/jo500316v