1-[2-(2-Phenyl-ethanesulfinyl)-phenyl]-1H-pyrrole | 140658-30-6

• 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-(2-Phenyl-ethanesulfinyl)-phenyl]-1H-pyrrole
• 英文别名: 1-[2-(2-Phenylethylsulfinyl)phenyl]pyrrole
• CAS: 140658-30-6
• 化学式: C₁₈H₁₇NOS
• 分子量: 295.405
• InChiKey: QAISLAQVFNWSSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-(2-Phenyl-ethanesulfinyl)-phenyl]-1H-pyrrole 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 1-Pyrrolo<2,1-b>benzothiazolecarboxylic acid
  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