(E)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (E)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
• 英文别名: E-BOX A；(2E)-2-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)acetamide
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: OUFUEOCARHOWCD-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴-4-甲基呋喃-2,5-二酮 在 bis-triphenylphosphine-palladium(II) chloride 、 ammonium hydroxide 、 ammonium acetate 、 水 、 乙酸酐 、 溶剂黄146 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 528.0h， 生成 (E)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
  参考文献：
  名称：

  Total Synthesis and Detection of the Bilirubin Oxidation Product (Z)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide (Z-BOX A)

  摘要：

  The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.

  DOI：

  10.1021/ol402221b

文献信息

• Total Synthesis and Detection of the Bilirubin Oxidation Product (<i>Z</i>)-2-(3-Ethenyl-4-methyl-5-oxo-1,5-dihydro-2<i>H</i>-pyrrol-2-ylidene)ethanamide (<i>Z</i>-BOX A)
  作者：Maurice Klopfleisch、Raphael A. Seidel、Helmar Görls、Hannes Richter、Rainer Beckert、Wolfgang Imhof、Markus Reiher、Georg Pohnert、Matthias Westerhausen

  DOI：10.1021/ol402221b

  日期：2013.9.6

  The selective total synthesis of the pure Z-isomer of BOX A (8a), a product of oxidative heme degradation with significant physiological impact, was achieved in four to six steps starting from 3-bromo-4-methylfuran-2,5-dione (1). Z-BOX A forms a strong hydrogen bridge framework in the crystalline state. LC-MS techniques allow identification and characterization of isomeric forms of BOX A.