ethyl 4-acetyl-1-[(aminocarbonyl)amino]-2-methyl-1H-pyrrole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-acetyl-1-[(aminocarbonyl)amino]-2-methyl-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 4-acetyl-1-[(aminocarbonyl)amino]-2-methyl-1H-3-pyrrolecarboxylate；Ethyl 4-acetyl-1-(carbamoylamino)-2-methylpyrrole-3-carboxylate
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: OGWQBOCPNSNXII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (4S*,5R*)-3-acetyl-1-[(aminocarbonyl)amino]-5-hydroxy-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate 在 CuCl₂*2H₂O 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以87%的产率得到ethyl 4-acetyl-1-[(aminocarbonyl)amino]-2-methyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Straightforward Entry into 5-Hydroxy-1-aminopyrrolines and the Corresponding Pyrroles from 1,2-Diaza-1,3-butadienes

  摘要：

  The synthesis of 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and 5-unsubstituted-1-aminopyrrole-3-carboxylic acid derivatives from 1,2-diaza-1,3-butadienes and aldehydes is presented. These domino reactions offer the advantage of executing multistep transformation without intermediate workup procedures. The stereoselectivity of ring closure to 5-hydroxy-1-aminopyrroline-3-carboxylic acid derivatives and phenyl transposition to 2,3-diphenyl-1-aminopyrrole-3-carboxylic acid derivatives are also studied.

  DOI：

  10.1021/jo025656k

文献信息

• 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
  作者：Orazio A. Attanasi、Gianfranco Favi、Paolino Filippone、Gianluca Giorgi、Fabio Mantellini、Giada Moscatelli、Domenico Spinelli

  DOI：10.1021/ol800557h

  日期：2008.5.1

  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.