2,2,2-trichloro-1-(4-bromo-5-fluoro-1H-pyrrol-2-yl)ethanone | 1352649-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloro-1-(4-bromo-5-fluoro-1H-pyrrol-2-yl)ethanone
• 英文别名: 1-(4-bromo-5-fluoro-1H-pyrrol-2-yl)-2,2,2-trichloroethanone
• CAS: 1352649-66-1
• 化学式: C₆H₂BrCl₃FNO
• 分子量: 309.349
• InChiKey: HHQBQXAPYASFBY-UHFFFAOYSA-N

物化性质

• 沸点：
  354.3±42.0 °C(Predicted)
• 密度：
  2.010±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-1-(4-bromo-5-fluoro-1H-pyrrol-2-yl)ethanone 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 fluorohymenidin formate
  参考文献：
  名称：

  Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

  摘要：

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.

  DOI：

  10.1021/ol2029993
• 作为产物：
  描述：

  1-(4-溴-1H-吡咯-2-基)-2,2,2-三氯-1-乙酮 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以42%的产率得到2,2,2-trichloro-1-(4-bromo-5-fluoro-1H-pyrrol-2-yl)ethanone
  参考文献：
  名称：

  Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin

  摘要：

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.

  DOI：

  10.1021/ol2029993

文献信息

• Microwave-Assisted Fluorination of 2-Acylpyrroles: Synthesis of Fluorohymenidin
  作者：Benjamin Troegel、Thomas Lindel

  DOI：10.1021/ol2029993

  日期：2012.1.20

  Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 degrees C in DMF.