ethyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-4-oxo-5-hexenoate | 1027008-17-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-4-oxo-5-hexenoate
• CAS: 1027008-17-8
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: KASQDGRRAWRAGW-BXEJXYHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120.08
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-4-oxo-5-hexenoate 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到ethyl 1-[(aminocarbonyl)amino]-5-[(E)-2-methoxy-1-ethenyl]-2-methyl-1H-3-pyrrolecarboxylate
  参考文献：
  名称：

  Flexible Protocol for the Chemo- and Regioselective Building of Pyrroles and Pyrazoles by Reactions of Danishefsky’s Dienes with 1,2-Diaza-1,3-butadienes

  摘要：

  The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky's diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4H-1-aminopyrroles and 4,5H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as a matter of fact, R-1 = COOR or CONR2 differently affects the acidity of the proton at the adjacent carbon. An unexpected formation of 5H-1-aminopyrroles from the reactions carried out in water was also observed.

  DOI：

  10.1021/ol800557h
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 ethyl 3-[(aminocarbonyl)diazenyl]but-2-enoate 在 zinc(II) chloride 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 以85%的产率得到ethyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-4-oxo-5-hexenoate
  参考文献：
  名称：

  Flexible Protocol for the Chemo- and Regioselective Building of Pyrroles and Pyrazoles by Reactions of Danishefsky’s Dienes with 1,2-Diaza-1,3-butadienes

  摘要：

  The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky's diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4H-1-aminopyrroles and 4,5H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as a matter of fact, R-1 = COOR or CONR2 differently affects the acidity of the proton at the adjacent carbon. An unexpected formation of 5H-1-aminopyrroles from the reactions carried out in water was also observed.

  DOI：

  10.1021/ol800557h