1-<2-(ethylsulfinyl)benzoyl>pyrrole | 141508-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<2-(ethylsulfinyl)benzoyl>pyrrole
• 英文别名: 2-(2-ethylsulfinyl)benzoyl pyrrole；(2-Ethylsulfinylphenyl)-pyrrol-1-ylmethanone
• CAS: 141508-13-6
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: SESJMACKXBPNMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-<2-(ethylsulfinyl)benzoyl>pyrrole 在 乙酸酐 、 copper(II) nitrate 作用下， 以 xylene 为溶剂， 反应 5.5h， 生成 1-nitropyrrolo<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
• 作为产物：
  描述：

  o-ethylmercapto-benzamine 在 sodium periodate 、 Amberlyst A-21 resin 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 66.0h， 生成 1-<2-(ethylsulfinyl)benzoyl>pyrrole
  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

• Pyrrolo(1,2-b)-(1,2)-benzothiazin-10-one and its use as an antimicrobial
  申请人：The Dow Chemical Company

  公开号：US05270307A1

  公开（公告）日：1993-12-14

  Pyrrolo-(1,2-b)-(1,2)-benzothiazin-10-one is prepared which corresponds to the formula: ##STR1## This compound has been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing this compound are so employed.

  制备了对应于以下式子的吡咯-(1,2-b)-(1,2)-苯并噻唑-10-酮：##STR1## 发现该化合物在工业和商业应用中表现出抗微生物活性，并且含有该化合物的组合物被应用于此类用途。
• PYRROLO(1,2-B)-(1,2)-BENZOTHIAZIN-10-ONE AND ITS USE AS AN ANTIMICROBIAL
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0643713A1

  公开（公告）日：1995-03-22
• US5270307A
  申请人：——

  公开号：US5270307A

  公开（公告）日：1993-12-14
• [EN] PYRROLO(1,2-B)-(1,2)-BENZOTHIAZIN-10-ONE AND ITS USE AS AN ANTIMICROBIAL<br/>[FR] PYRROLO(1,2-B)-(1,2)-BENZOTHIAZINE-10-ONE ET SON UTILISATION EN TANT QU'ANTI-MICROBIEN
  申请人：THE DOW CHEMICAL COMPANY

  公开号：WO1994022876A1

  公开（公告）日：1994-10-13

  (EN) Pyrrolo-(1,2-b)-(1,2)-benzothiazin-10-one is prepared which corresponds to formula (I). This compound has been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing this compound are so employed.(FR) Pyrrolo (1,2-B)-(1,2)-benzothiazine-10-one est préparé selon la formule (I). Il a été constaté que ce composé présente une activité anti-microbienne dans ses applications commerciales et industrielles. Des compositions contenant ce composé sont utilisées à des fins anti-microbiennes.
• 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.