1-formylpyrrolo<2,1-b><1,3>benzothiazin-9-one | 141508-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1-formylpyrrolo<2,1-b><1,3>benzothiazin-9-one
• 英文别名: 9-oxopyrrolo[2,1-b][1,3]benzothiazine-1-carbaldehyde
• CAS: 141508-16-9
• 化学式: C₁₂H₇NO₂S
• 分子量: 229.259
• InChiKey: YXAVZRFZXVHSOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.55
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-<2-(ethylsulfinyl)benzoyl>pyrrole 在 三氯氧磷 作用下， 以 xylene 为溶剂， 反应 2.75h， 生成 1-formylpyrrolo<2,1-b><1,3>benzothiazin-9-one
  参考文献：
  名称：

  Intramolecular capture of Pummerer rearrangement intermediates. IV. Preparation of pyrrolo[2,1-b][1,3]benzothiazin-9-ones via intramolecular sulfenylation of an N-acylpyrrole

  摘要：

  Pyrrolo[2,1-b][1,3]benzothiazin-9-one (6a) was synthesized in 45% overall yield from thiosalicylic acid in six steps. The title compound (88%) and its 1-trifluoroacetyl (83%) and 1-formyl derivatives were synthesized via intramolecular reaction of 1-(2-ethylsulfinyl)benzoylpyrrole (5) by thermal cyclization or treatment with trifluoroacetic anhydride or DMF/POCl3, respectively. The key step in each can is formation of the heterocycle by sulfoxide activation followed by C-S bond formation via attack at sulfur. Reaction of 6a with common electrophiles (trifluoroacetic anhydride (86%), POCl3/DMF (75%), and acetyl nitrate) indicates that C-1 is the predominant site of electrophilic substitution.

  DOI：

  10.1021/jo00039a030

文献信息

• Intramolecular capture of Pummerer rearrangement intermediates. IV. Preparation of pyrrolo[2,1-b][1,3]benzothiazin-9-ones via intramolecular sulfenylation of an N-acylpyrrole
  作者：Kelley A. Tafel、Dallas K. Bates

  DOI：10.1021/jo00039a030

  日期：1992.6

  Pyrrolo[2,1-b][1,3]benzothiazin-9-one (6a) was synthesized in 45% overall yield from thiosalicylic acid in six steps. The title compound (88%) and its 1-trifluoroacetyl (83%) and 1-formyl derivatives were synthesized via intramolecular reaction of 1-(2-ethylsulfinyl)benzoylpyrrole (5) by thermal cyclization or treatment with trifluoroacetic anhydride or DMF/POCl3, respectively. The key step in each can is formation of the heterocycle by sulfoxide activation followed by C-S bond formation via attack at sulfur. Reaction of 6a with common electrophiles (trifluoroacetic anhydride (86%), POCl3/DMF (75%), and acetyl nitrate) indicates that C-1 is the predominant site of electrophilic substitution.