1-<2-(Ethylsulfinyl)phenyl>pyrrole | 107344-55-8

• 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-(Ethylsulfinyl)phenyl>pyrrole
• 英文别名: N-(2-ethylsulfinylphenyl)pyrrole；1-(2-(Ethylsulfinyl)phenyl)-1H-pyrrole；1-(2-ethylsulfinylphenyl)pyrrole
• CAS: 107344-55-8
• 化学式: C₁₂H₁₃NOS
• 分子量: 219.307
• InChiKey: OFXFMUITSLKRMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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：
  41.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<2-(Ethylsulfinyl)phenyl>pyrrole 在 乙酸酐 、 三氟乙酸酐 作用下， 反应 2.5h， 以70%的产率得到Pyrrolo<2,1-b>benzothiazol
  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
• 作为产物：
  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：

文献信息

• 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：——
• BATES, D. K.;SELL, B. A.;PICARD, J. A., TETRAHEDRON LETT., 28,(1987) N 31, 3535-3538
  作者：BATES, D. K.、SELL, B. A.、PICARD, J. A.

  DOI：——

  日期：——
• An interrupted pummerer reaction induced by vilsmeier reagent (POCl3/DMF)1
  作者：Dallas K. Bates、Burnell A. Sell、Joseph A. Picard

  DOI：10.1016/s0040-4039(00)95528-x

  日期：1987.1
• 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：——
• 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.