2-{(5E)-2-[(diethylamino)carbonyl]-6-methoxy-1-methyl-4-oxo-5-hexenylidene}-1-hydrazinecarboxamide | 1027008-27-0

• 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: 2-{(5E)-2-[(diethylamino)carbonyl]-6-methoxy-1-methyl-4-oxo-5-hexenylidene}-1-hydrazinecarboxamide
• CAS: 1027008-27-0
• 化学式: C₁₄H₂₄N₄O₄
• 分子量: 312.369
• InChiKey: AKGWAGWVNHXPFI-CEPXYSCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  114.09
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{(5E)-2-[(diethylamino)carbonyl]-6-methoxy-1-methyl-4-oxo-5-hexenylidene}-1-hydrazinecarboxamide 在 Amberlyst 15 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到3-{2-[(diethylamino)carbonyl]-3-oxobutyl}-1H-1-pyrazolecarboxamide
  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 、 2-(4-(diethylamino)-4-oxobut-2-en-2-yl)diazene-1-carboxamide 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83%的产率得到2-{(5E)-2-[(diethylamino)carbonyl]-6-methoxy-1-methyl-4-oxo-5-hexenylidene}-1-hydrazinecarboxamide
  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