pyrrolo<2,1-b><1,3>benzothiazin-9-one | 141508-14-7

• 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: pyrrolo<2,1-b><1,3>benzothiazin-9-one
• 英文别名: pyrrolo(2,1-b)-(1,3)benzothiazin-9-one；Benzo[e]pyrrolo[2,1-b][1,3]thiazin-9-one；pyrrolo[2,1-b][1,3]benzothiazin-9-one
• CAS: 141508-14-7
• 化学式: C₁₁H₇NOS
• 分子量: 201.249
• InChiKey: PWVSBZMBOBCLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyrrolo<2,1-b><1,3>benzothiazin-9-one 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以75%的产率得到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
• 作为产物：
  描述：

  1-<2-(ethylsulfinyl)benzoyl>pyrrole 在 2-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 以20%的产率得到pyrrolo<2,1-b><1,3>benzothiazin-9-one
  参考文献：
  名称：

  Pyrrolo(1,2-b)-(1,2)-benzothiazin-10-one and its use as an antimicrobial

  摘要：

  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。

  公开号：

  US05270307A1

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。
• Sulfenylation Using Sulfoxides. Intramolecular Cyclization of 2- and 3-Acylpyrroles
  作者：Dallas K. Bates、Kelley A. Tafel

  DOI：10.1021/jo00105a026

  日期：1994.12

  AlCl3-catalyzed acylation of N-(phenylsulfonyl)pyrrole with 2-(ethylthio)benzoyl chloride followed by hydrolysis provided 2-(2-(ethylthio)benzoyl)pyrrole (3). Compound 3 was also available from ethyl 2-(ethylthio)benzoate and pyrrolylmagnesium chloride (Scheme 2). Oxidation(NaIO4) gave the corresponding sulfoxide 4 which when refluxed 6 h inp-xylene (bp 138 degrees C) gave predominately the C-3 cyclization product 11 (51%) along with the rearrangement product 12 (17%). Conducting the thermal reaction in the presence of DMAP in refluxing toluene gave mainly the N-1 cyclization product 13 (46%) also accompanied by the rearrangement product 12 (20%). Formation of a 2H-pyrrole spirocyclic intermediate from thermally promoted intramolecular ipso-sulfenylation in 4 is suggested to account for the formation of 12. The N-methyl derivative of 4 (i.e. 6) produced 9 and 10 after 9 h at 138 degrees C; in the presence of DMAP only 9 is produced after 18 h at 138 degrees C. The 3-acyl sulfoxide 8 cyclized to 17 during 6.5 h at 138 degrees C. These results indicate that although sulfoxides are useful for intramolecular sulfenylation reactions, care must be taken in assigning structures to the product(s) because rearrangement may take place during and/or after the initial cyclization reaction. Addition of a basic amine to the reaction mixture may prevent acid-catalyzed rearrangements of the initially formed products.
• 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.