2-[(4-methylphenyl)sulfanyl]pyridinium-N-(4-fluorophenyl)imide | 569338-71-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-methylphenyl)sulfanyl]pyridinium-N-(4-fluorophenyl)imide
• 英文别名: (4-Fluorophenyl)-[2-(4-methylphenyl)sulfanylpyridin-1-ium-1-yl]azanide
• CAS: 569338-71-2
• 化学式: C₁₈H₁₅FN₂S
• 分子量: 310.395
• InChiKey: BODRSIAQLSAITI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-methylphenyl)sulfanyl]pyridinium-N-(4-fluorophenyl)imide 以 氯仿 为溶剂， 反应 2.0h， 生成 (3aR,4aS,8aS,8bS)-rel-4-(4-fluorophenyl)-7-[(4-methylphenyl)sulfanyl]-2-phenyl-3b,4a,8a,8b-tetrahydro-1H-pyrrolo[3',4':4,5]-1H-pyrrolo[3,2-b]pyridine-1,3(2H)-dione
  参考文献：
  名称：

  Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives. Fused Azolium Salts. 22

  摘要：

  2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.

  DOI：

  10.1021/jo034231a
• 作为产物：
  描述：

  4-Methyl-benzenethiol anion 、 3-(4-fluorophenyl)tetrazolo[1,5-a]pyridinium tetrafluoroborate 以82%的产率得到2-[(4-methylphenyl)sulfanyl]pyridinium-N-(4-fluorophenyl)imide
  参考文献：
  名称：

  Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives. Fused Azolium Salts. 22

  摘要：

  2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.

  DOI：

  10.1021/jo034231a

文献信息

• Unexpected Ring Transformation to Pyrrolo[3.2-<i>b</i>]pyridine Derivatives. Fused Azolium Salts. 22
  作者：Zsuzsanna Riedl、Péter Kövér、Tibor Soós、György Hajós、Orsolya Egyed、László Fábián、András Messmer

  DOI：10.1021/jo034231a

  日期：2003.7.1

  2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.