2-<2-(Ethylsulfinyl)benzoyl>pyrrole | 153716-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<2-(Ethylsulfinyl)benzoyl>pyrrole
• 英文别名: 2-(2-Ethylsulfinyl)benzoyl pyrrole；(2-ethylsulfinylphenyl)-(1H-pyrrol-2-yl)methanone
• CAS: 153716-46-2
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: KUVJOLCCKRCZAN-UHFFFAOYSA-N

物化性质

• 沸点：
  491.1±25.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<2-(Ethylsulfinyl)benzoyl>pyrrole 以 xylene 为溶剂， 反应 6.0h， 以17%的产率得到pyrrolo<2,1-b><1,3>benzothiazin-9-one
  参考文献：
  名称：

  Sulfenylation Using Sulfoxides. Intramolecular Cyclization of 2- and 3-Acylpyrroles

  摘要：

  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.

  DOI：

  10.1021/jo00105a026
• 作为产物：
  描述：

  2-ethylsulfanyl benzoic acid chloride 在 氢氧化钾 、 sodium periodate 、 三氯化铝 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 26.0h， 生成 2-<2-(Ethylsulfinyl)benzoyl>pyrrole
  参考文献：
  名称：

  Sulfenylation Using Sulfoxides. Intramolecular Cyclization of 2- and 3-Acylpyrroles

  摘要：

  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.

  DOI：

  10.1021/jo00105a026

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Pyrrolo-(1,2-b)-(1,2)-benzothiazin-10-one，其化学式为：##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，含有该化合物的组合物被用于这些应用中。
• 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.