2-bromo-3-methoxy-2-propenenitrile

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromo-3-methoxy-2-propenenitrile
• 英文别名: (E)-2-bromo-3-methoxyprop-2-enenitrile
• 化学式: C₄H₄BrNO
• 分子量: 161.986
• InChiKey: SUEQYOPZPLDCPW-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-3-methoxy-2-propenenitrile 、 N-Butyl-pentanamidine 在 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 18.0h， 以45%的产率得到2,3-Dibutyl-3H-imidazole-4-carbonitrile
  参考文献：
  名称：

  A New Regioselective Synthesis of 1,2,5-Trisubstituted 1H-Imidazoles and Its Application to the Development of Eprosartan

  摘要：

  A new method is presented for the preparation of 1,2-disubstitued-1H-imidazole-5-carboxaldehydes by the reaction of N-monosubstituted amidines with 2-halo-3-alkoxy-2-propenals. The reaction is highly regioselective with ratios of 1,2,5:1,2,4-imidazolecarboxaldehydes ranging from 85:15 to 100: 0. This methodology could be extended with similar results to the synthesis of imidazole-g-nitriles by the reaction of 2-bromo-3-methoxy-2-propenenitrile with N-monosubstituted amidines.

  DOI：

  10.1021/jo971304f

文献信息

• A New Regioselective Synthesis of 1,2,5-Trisubstituted 1<i>H</i>-Imidazoles and Its Application to the Development of Eprosartan
  作者：Susan C. Shilcrat、Mohamed K. Mokhallalati、Joseph M. D. Fortunak、Lendon N. Pridgen

  DOI：10.1021/jo971304f

  日期：1997.11.1

  A new method is presented for the preparation of 1,2-disubstitued-1H-imidazole-5-carboxaldehydes by the reaction of N-monosubstituted amidines with 2-halo-3-alkoxy-2-propenals. The reaction is highly regioselective with ratios of 1,2,5:1,2,4-imidazolecarboxaldehydes ranging from 85:15 to 100: 0. This methodology could be extended with similar results to the synthesis of imidazole-g-nitriles by the reaction of 2-bromo-3-methoxy-2-propenenitrile with N-monosubstituted amidines.