N-benzenesulfonyl-3-bromo-2-iodopyrrole | 1229516-55-5

• 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: N-benzenesulfonyl-3-bromo-2-iodopyrrole
• 英文别名: 1-(Benzenesulfonyl)-3-bromo-2-iodopyrrole
• CAS: 1229516-55-5
• 化学式: C₁₀H₇BrINO₂S
• 分子量: 412.046
• InChiKey: FDAQYENLGRLLTL-UHFFFAOYSA-N

物化性质

• 熔点：
  75.5-76.5 °C(Solvent: Diethyl ether; Pentane)
• 沸点：
  488.3±48.0 °C(predicted)
• 密度：
  2.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯磺酰基-3-溴吡咯 在 正丁基锂 、 二异丙胺 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以99%的产率得到N-benzenesulfonyl-3-bromo-2-iodopyrrole
  参考文献：
  名称：

  Directed Lithiation of N-Benzenesulfonyl-3-bromopyrrole. Electrophile-Controlled Regioselective Functionalization via Dynamic Equilibrium between C-2 and C-5 Lithio Species

  摘要：

  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,

  DOI：

  10.1021/ol100810c

文献信息

• 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.