2-(3-甲基-5-氧代-4-乙烯基-1,5-二氢-2H-吡咯-2-亚基)乙酰胺 | 329314-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 2-(3-甲基-5-氧代-4-乙烯基-1,5-二氢-2H-吡咯-2-亚基)乙酰胺
• 英文名称: 2-(4-ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide
• 英文别名: BOX B；2-(4-Ethenyl-3-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)acetamide；2-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)acetamide
• CAS: 329314-75-2
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: JJDLLVZMTMEVBY-UHFFFAOYSA-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：

  bilirubin IXα 在 水 、 双氧水 、 sodium chloride 作用下， 生成 (Z)-2-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)ethanamide 、 2-(3-甲基-5-氧代-4-乙烯基-1,5-二氢-2H-吡咯-2-亚基)乙酰胺
  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

• <i>In vivo</i>and<i>in vitro</i>identification of<i>Z</i>-BOX C – a new bilirubin oxidation end product
  作者：Marcel Ritter、Sandesh Neupane、Raphael A. Seidel、Christoph Steinbeck、Georg Pohnert

  DOI：10.1039/c8ob00164b

  日期：——

  A new bilirubin oxidation end product (BOX) was isolated and characterized. The formation of the so-called Z-BOX C proceeds from bilirubin via propentdyopents as intermediates. This BOX was detected in pathological human bile samples using liquid chromatography/mass spectrometry and has potential relevance for liver dysfunction and cerebral vasospasms.

  分离并表征了新的胆红素氧化终产物（BOX）。所谓的Z - BOX C的形成是从胆红素经propentdyopents作为中间体进行的。使用液相色谱/质谱法在病理性人胆汁样品中检测到该BOX，它与肝功能障碍和脑血管痉挛具有潜在的相关性。
• 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.