ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate | 1307916-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate
• 英文别名: Ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate
• CAS: 1307916-25-1
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: HUNRYAMWGBGXSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Efficient syntheses of ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate

  摘要：

  Ethyl 2-chloroacetoacetate and its 4-chloro isomer react with cyanoacetamide in the presence of the mild, nonnucleophilic base, triethylamine under stoichiometric conditions to give high yields of ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate and ethyl (4-cyano-2-hydroxy-5-oxopyrrolidin-2-yl)acetate, respectively. These, under acid-catalyzed dehydration conditions, afforded ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate, respectively. Similarly, the 4-chloro isomer reacted with ethyl cyanoacetate to give the novel product, diethyl 2-cyano-4-oxohexanedioate. The use of triethylamine enables access to a whole new library of pyrrole derivatives from easily accessible, commercially available starting materials. The reactions described in this Letter enable access to libraries of important pyrrole systems in any of the isotopically enriched forms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.025
• 作为产物：
  描述：

  2-氯乙酰乙酸乙酯 、 氰乙酰胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Efficient syntheses of ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate

  摘要：

  Ethyl 2-chloroacetoacetate and its 4-chloro isomer react with cyanoacetamide in the presence of the mild, nonnucleophilic base, triethylamine under stoichiometric conditions to give high yields of ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate and ethyl (4-cyano-2-hydroxy-5-oxopyrrolidin-2-yl)acetate, respectively. These, under acid-catalyzed dehydration conditions, afforded ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate, respectively. Similarly, the 4-chloro isomer reacted with ethyl cyanoacetate to give the novel product, diethyl 2-cyano-4-oxohexanedioate. The use of triethylamine enables access to a whole new library of pyrrole derivatives from easily accessible, commercially available starting materials. The reactions described in this Letter enable access to libraries of important pyrrole systems in any of the isotopically enriched forms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.025

文献信息

• Efficient syntheses of ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate
  作者：Prativa B.S. Dawadi、Johan Lugtenburg

  DOI：10.1016/j.tetlet.2011.03.025

  日期：2011.5

  Ethyl 2-chloroacetoacetate and its 4-chloro isomer react with cyanoacetamide in the presence of the mild, nonnucleophilic base, triethylamine under stoichiometric conditions to give high yields of ethyl 4-cyano-2-hydroxy-2-methyl-5-oxopyrrolidine-3-carboxylate and ethyl (4-cyano-2-hydroxy-5-oxopyrrolidin-2-yl)acetate, respectively. These, under acid-catalyzed dehydration conditions, afforded ethyl 4-cyano-5-hydroxy-2-methyl-1H-pyrrole-3-carboxylate and ethyl (2Z)-(4-cyano-5-oxopyrrolidin-2-ylidene)ethanoate, respectively. Similarly, the 4-chloro isomer reacted with ethyl cyanoacetate to give the novel product, diethyl 2-cyano-4-oxohexanedioate. The use of triethylamine enables access to a whole new library of pyrrole derivatives from easily accessible, commercially available starting materials. The reactions described in this Letter enable access to libraries of important pyrrole systems in any of the isotopically enriched forms. (C) 2011 Elsevier Ltd. All rights reserved.