methyl [2-(2Z)-(3-ethenyl-4-methyl-5-oxofuran-2(5H)-ylidene)]ethanoate | 1451878-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: methyl [2-(2Z)-(3-ethenyl-4-methyl-5-oxofuran-2(5H)-ylidene)]ethanoate
• 英文别名: methyl (2Z)-2-(3-ethenyl-4-methyl-5-oxofuran-2-ylidene)acetate
• CAS: 1451878-31-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: LHNPWTWBYPWHHS-YVMONPNESA-N

物化性质

• 沸点：
  327.9±35.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl [2-(2Z)-(3-ethenyl-4-methyl-5-oxofuran-2(5H)-ylidene)]ethanoate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 10.0h， 以84%的产率得到methyl [2-(2Z)-(3-ethenyl-4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)]ethanoate
  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
• 作为产物：
  描述：

  3-溴-4-甲基呋喃-2,5-二酮 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.0h， 生成 methyl [2-(2Z)-(3-ethenyl-4-methyl-5-oxofuran-2(5H)-ylidene)]ethanoate
  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