N-benzenesulfonyl-3-bromo-2-(phenylthio)pyrrole | 1229516-53-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-benzenesulfonyl-3-bromo-2-(phenylthio)pyrrole
• 英文别名: 1-(Benzenesulfonyl)-3-bromo-2-phenylsulfanylpyrrole；1-(benzenesulfonyl)-3-bromo-2-phenylsulfanylpyrrole
• CAS: 1229516-53-3
• 化学式: C₁₆H₁₂BrNO₂S₂
• 分子量: 394.313
• InChiKey: MQAGICSHUQCSGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(苯基磺酰基)吡咯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 三氟甲磺酸 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.5h， 生成 N-benzenesulfonyl-3-bromo-2-(phenylthio)pyrrole
  参考文献：
  名称：

  Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole

  摘要：

  The regioselective bromine-lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 with n-BuLi and diisopropylamine followed by quenching with electrophiles produced regioisomeric 2-substituted 3-bromopyrroles (3) selectively. The latter reaction can be rationalized by the rapid equilibration of the C-5 lithio species (4) to the more stable C-2 lithio species (2) in the presence of diisopropylamine.

  DOI：

  10.3987/com-12-s(n)81

文献信息

• Directed Lithiation of <i>N</i>-Benzenesulfonyl-3-bromopyrrole. Electrophile-Controlled Regioselective Functionalization via Dynamic Equilibrium between C-2 and C-5 Lithio Species
  作者：Tsutomu Fukuda、Takeshi Ohta、Ei-ichi Sudo、Masatomo Iwao

  DOI：10.1021/ol100810c

  日期：2010.6.18

  Directed lithiation of N-benzenesulfonyl-3-bromopyrrole (1) with LDA in THF at -78 degrees C generated C-2 lithio species 3 selectively. Reactions of 3 with reactive electrophiles produced the corresponding 2-functionalized pyrroles 4. On the other hand, quenching with less reactive electrophiles generated the corresponding 5-substituted pyrroles 5. The latter unusual functionalization at C-5 could be rationalized by dynamic equilibrium between C-2 and C-5 lithio species,
• Optional Synthesis of 2- or 5-Substituted 3-Bromopyrroles via Bromine-Lithium Exchange of N-Benzenesulfonyl-2,4-dibromopyrrole
  作者：Masatomo Iwao、Tsutomu Fukuda

  DOI：10.3987/com-12-s(n)81

  日期：——

  The regioselective bromine-lithium exchange of N-benzenesulfonyl-2,4-dibromopyrrole (6) with n-BuLi followed by treatment with various electrophiles gave 5-substituted 3-bromopyrroles (5) in excellent yields. In contrast, the sequential treatment of 6 with n-BuLi and diisopropylamine followed by quenching with electrophiles produced regioisomeric 2-substituted 3-bromopyrroles (3) selectively. The latter reaction can be rationalized by the rapid equilibration of the C-5 lithio species (4) to the more stable C-2 lithio species (2) in the presence of diisopropylamine.