methyl 4-bromo-1-[2-methoxycarbonyl-6-(trifluoromethyl)-phenyl]-1H-pyrrole-2-carboxylate | 1376707-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-bromo-1-[2-methoxycarbonyl-6-(trifluoromethyl)-phenyl]-1H-pyrrole-2-carboxylate
• 英文别名: Methyl 4-bromo-1-[2-methoxycarbonyl-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylate
• CAS: 1376707-76-4
• 化学式: C₁₅H₁₁BrF₃NO₄
• 分子量: 406.156
• InChiKey: MXBMZRFUFANIDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (R)-(+)-1-[2-methoxycarbonyl-6-(trifluoromethyl)phenyl]-pyrrole-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以98%的产率得到methyl 4-bromo-1-[2-methoxycarbonyl-6-(trifluoromethyl)-phenyl]-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Useful, regioflexible methods for functionalization of 1-phenylpyrrole derivatives

  摘要：

  Highly regioselective mono-, di- and tribrominations of 1-[2-(trifluoromethyl)phenyl]-1H-pyrrole and several derivatives were accomplished with N-bromosuccinimide under mild conditions. Combined applications of these brominations with organometallic (e.g., bromine/lithium exchange or metalation) reactions provided a novel regioflexible route to new multifunctionalised 1-phenylpyrrole derivatives. The structures of the new products were determined by spectroscopic methods and confirmed in three cases with single crystal X-ray diffraction measurements. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.070