4,5-dibromo-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide | 334707-24-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5-dibromo-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide
• CAS: 334707-24-3
• 化学式: C₁₂H₁₄Br₂N₄O₃
• 分子量: 422.076
• InChiKey: UMHOECCQNHAZEY-UHFFFAOYSA-N

物化性质

• 密度：
  1.771±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到midpacamide
  参考文献：
  名称：

  A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids

  摘要：

  A two-step synthesis of the N-acylated alpha -azido-omega -aminovalerate. a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding alpha -ureido ester derivative to give the 3-methylhydantoin ring present in midpacamide, whereas the reaction with triphenylphosphine. tosyl isocyanate and ammonia followed by cyclization of the resulting guanidine derivative provides the 2-aminoimidazole ring present in dispacamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02120-1
• 作为产物：
  描述：

  在 sodium hydroxide 、 水 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4,5-dibromo-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids

  摘要：

  A two-step synthesis of the N-acylated alpha -azido-omega -aminovalerate. a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding alpha -ureido ester derivative to give the 3-methylhydantoin ring present in midpacamide, whereas the reaction with triphenylphosphine. tosyl isocyanate and ammonia followed by cyclization of the resulting guanidine derivative provides the 2-aminoimidazole ring present in dispacamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02120-1