4,5-dibromo-N-[3-(1,3-dihydro-2-imidazolon-4-yl)-3-methoxylpropyl]-1H-pyrrole-2-carboxamide | 441045-32-5

• 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-(1,3-dihydro-2-imidazolon-4-yl)-3-methoxylpropyl]-1H-pyrrole-2-carboxamide
• 英文别名: 4,5-dibromo-N-[3-methoxy-3-(2-oxo-1,3-dihydroimidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide
• CAS: 441045-32-5
• 化学式: C₁₂H₁₄Br₂N₄O₃
• 分子量: 422.076
• InChiKey: CWJQWMSDPBVVIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-N-[3-(1,3-dihydro-2-imidazolon-4-yl)-3-methoxylpropyl]-1H-pyrrole-2-carboxamide 在 palladium on activated charcoal 氢气 、 溴 、 sodium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 32.0h， 生成 4-(2,4-dioxoimidazolidin-5-yl)-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]azepin-8-one
  参考文献：
  名称：

  Synthesis of Axinohydantoins

  摘要：

  A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.

  DOI：

  10.1021/jo020063v
• 作为产物：
  描述：

  4-(3-aminopropyl)-1,3-dihydro-2-imidazolone 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 4,5-dibromo-N-[3-(1,3-dihydro-2-imidazolon-4-yl)-3-methoxylpropyl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis of Axinohydantoins

  摘要：

  A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.

  DOI：

  10.1021/jo020063v

文献信息

• Synthesis of Axinohydantoins
  作者：Ana Carolina Barrios Sosa、Kenichi Yakushijin、David A. Horne

  DOI：10.1021/jo020063v

  日期：2002.6.1

  A short synthesis of the hydantoin-containing marine sponge metabolites axinohydantoins is described. A key feature of the synthesis is a putative biomimetic, intramolecular cyclization of alpha-functionalized imidazolone 5, which affords the tricyclic pyrroloazepinone framework comprising 6. In addition, the conversion of imidazolones to alpha,beta-unsaturated hydantoins is outlined and represents a new approach to these heterocyclic systems.