1-<2-(Ethylthio)phenyl>pyrrole | 107344-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-<2-(Ethylthio)phenyl>pyrrole
• 英文别名: 1-(2-ethylthiophenyl)pyrrole；N-(2-ethylthiophenyl)pyrrole；1-[2-(Ethylsulfanyl)phenyl]-1H-pyrrole；1-(2-ethylsulfanylphenyl)pyrrole
• CAS: 107344-51-4
• 化学式: C₁₂H₁₃NS
• 分子量: 203.308
• InChiKey: BSPKWWAEUIWACN-UHFFFAOYSA-N

物化性质

• 沸点：
  315.2±25.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-<2-(Ethylthio)phenyl>pyrrole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到1-<2-(Ethylsulfinyl)phenyl>pyrrole
  参考文献：
  名称：

  Bates, Dallas K.; Winters, R. Thomas; Burnell, A. Sell, Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 695 - 699

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 2-(乙硫基)苯胺 在 溶剂黄146 作用下， 反应 2.25h， 以55%的产率得到1-<2-(Ethylthio)phenyl>pyrrole
  参考文献：
  名称：

  Intramolecular capture of Pummerer rearrangement intermediates. 3. Interrupted Pummerer rearrangement: capture of tricoordinate sulfur species generated under Pummerer rearrangement conditions

  摘要：

  A new approach to fused N,S-heterocycles is described. Treatment of N-(2-(alkylsulfinyl)phenyl)pyrroles (5) under conditions which typically promote reaction at the carbon a to the sulfoxide group (i.e., the TFAA-initiated Pummerer Rearrangement) produces selectively either pyrrolo[2,1-b]benzothiazole (9) or 1-(trifluoroacetyl)-pyrrolo[2,1-b]benzothiazole (7). It is suggested the process occurs by reaction of the pyrrole nucleus at sulfur of the corresponding O-trifluoroacetylated sulfoxide 1 producing an intermediate S-alkylpyrrolo[2,1-b]benzothiazolium salt 3. Nucleophilic displacement of the S-alkyl substituent by the trifluoroacetate counterion liberates pyrrolo[2,1-b]benzothiazole, which may undergo trifluoracetylation in the presence of excess TFAA. This approach to sulfur activation for intramolecular cyclizations is superior to other methods (usually involving positive halogen and a sulfide) since polyhalogenation and the instability of derivative halopyrroles are avoided.

  DOI：

  10.1021/jo00037a027

文献信息

• Bates, Dallas K.; Winters, R. Thomas; Burnell, A. Sell, Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 695 - 699
  作者：Bates, Dallas K.、Winters, R. Thomas、Burnell, A. Sell

  DOI：——

  日期：——
• Picard, Joseph A.; Chen, Shaowu; Bates, Dallas K., Heterocycles, 1994, vol. 38, # 8, p. 1775 - 1790
  作者：Picard, Joseph A.、Chen, Shaowu、Bates, Dallas K.

  DOI：——

  日期：——
• An Interrupted Pummerer Reaction Induced by Hypervalent Iodine(III) Reagent: A New Synthesis of Pyrrolo[2,1-b]benzothiazole
  作者：Ling-Ching Chen、Huey-Min Wang、Iou-Jiun Kang

  DOI：10.3987/com-99-8510

  日期：——

  Treatment of 1-(2-alkylthiophenyl)pyrroles with phenyliodine (III) bis(trifluoroacetate) containing trifluoroacetic acid resulted in an interrupted Pummerer reaction to give pyrrolo[2,1-b]benzothiazole rather than the normal Pummerer-type products.
• Intramolecular capture of Pummerer rearrangement intermediates. 3. Interrupted Pummerer rearrangement: capture of tricoordinate sulfur species generated under Pummerer rearrangement conditions
  作者：Dallas K. Bates、R. Thomas Winters、Joseph A. Picard

  DOI：10.1021/jo00037a027

  日期：1992.5

  A new approach to fused N,S-heterocycles is described. Treatment of N-(2-(alkylsulfinyl)phenyl)pyrroles (5) under conditions which typically promote reaction at the carbon a to the sulfoxide group (i.e., the TFAA-initiated Pummerer Rearrangement) produces selectively either pyrrolo[2,1-b]benzothiazole (9) or 1-(trifluoroacetyl)-pyrrolo[2,1-b]benzothiazole (7). It is suggested the process occurs by reaction of the pyrrole nucleus at sulfur of the corresponding O-trifluoroacetylated sulfoxide 1 producing an intermediate S-alkylpyrrolo[2,1-b]benzothiazolium salt 3. Nucleophilic displacement of the S-alkyl substituent by the trifluoroacetate counterion liberates pyrrolo[2,1-b]benzothiazole, which may undergo trifluoracetylation in the presence of excess TFAA. This approach to sulfur activation for intramolecular cyclizations is superior to other methods (usually involving positive halogen and a sulfide) since polyhalogenation and the instability of derivative halopyrroles are avoided.