tert-butyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-3,5-dimethyl-4-oxo-5-hexenoate | 1027008-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-3,5-dimethyl-4-oxo-5-hexenoate
• CAS: 1027008-35-0
• 化学式: C₁₆H₂₇N₃O₅
• 分子量: 341.407
• InChiKey: UIKDPVLPIJMOBQ-HNRQITJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  tert-butyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-3,5-dimethyl-4-oxo-5-hexenoate 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到tert-butyl 1-[(aminocarbonyl)amino]-5-[(E)-2-methoxy-1-methyl-1-ethenyl]-2,4-dimethyl-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：

  1-methoxy-2-methyl-3-trimethylsilyloxy-1,3-pentadiene 、 tert-butyl 3-(carbamoyldiazenyl)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94%的产率得到tert-butyl (E)-2-{1-[2-(aminocarbonyl)hydrazono]ethyl}-6-methoxy-3,5-dimethyl-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