[2-(1H-Pyrrol-1-yl)benzene-1-sulfinyl]acetonitrile | 107344-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [2-(1H-Pyrrol-1-yl)benzene-1-sulfinyl]acetonitrile
• 英文别名: 2-(2-pyrrol-1-ylphenyl)sulfinylacetonitrile
• CAS: 107344-57-0
• 化学式: C₁₂H₁₀N₂OS
• 分子量: 230.29
• InChiKey: RTRZIWSQLHWMNR-UHFFFAOYSA-N

物化性质

• 沸点：
  474.2±30.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-(1H-Pyrrol-1-yl)benzene-1-sulfinyl]acetonitrile 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 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：

  双(2-N-吡咯基苯基)二硫化物 在 氢氧化钾 、 间氯过氧苯甲酸 、 红铝 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 [2-(1H-Pyrrol-1-yl)benzene-1-sulfinyl]acetonitrile
  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

• 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.