4-(4′-methoxyphenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-selenazole | 1597438-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4′-methoxyphenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-selenazole
• 英文别名: Pentafluoro-[4-[4-(4-methoxyphenyl)-1,3-selenazol-2-yl]phenyl]-lambda6-sulfane；pentafluoro-[4-[4-(4-methoxyphenyl)-1,3-selenazol-2-yl]phenyl]-λ6-sulfane
• CAS: 1597438-02-2
• 化学式: C₁₆H₁₂F₅NOSSe
• 分子量: 440.295
• InChiKey: WKCXZCDRUYPXNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  25
• 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：
  23.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  五氟化(4-氰苯基)硫 在 Woollins 试剂 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 11.0h， 生成 4-(4′-methoxyphenyl)-2-(4″-pentafluorosulfanylphenyl)-1,3-selenazole
  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

文献信息

• 2,4-Diaryl-1,3-Chalcogen Azoles Bearing Pentafluorosulfanyl SF₅Groups: A Synthetic and Structural Study
  作者：Guoxiong Hua、Junyi Du、Alexandra M. Z. Slawin、J. Derek Woollins

  DOI：10.1021/jo500316v

  日期：2014.5.2

  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.