5-amino-2-oxo-1-(2-phenylethyl)-3H-pyrrole-4-carbonitrile | 1140352-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-amino-2-oxo-1-(2-phenylethyl)-3H-pyrrole-4-carbonitrile
• CAS: 1140352-16-4
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: LMCGQPRNQSAHAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-2-oxo-1-(2-phenylethyl)-3H-pyrrole-4-carbonitrile 、 丙烯酰氯 以 二氯甲烷 为溶剂， 以69%的产率得到3-[3-Cyano-2,5-dioxo-1-(2-phenylethyl)pyrrolidin-3-yl]propanamide
  参考文献：
  名称：

  Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams

  摘要：

  An effective route to novel polysubstituted imides is described, which involves the reaction of enamino-nitrile gamma-lactams derived from N-alkylated alpha-bromoacetamides and malononitrile with acryloyl chloride derivatives. This preceded via a sequence 1,4-addition-intramolecular peptidic coupling and a gamma-lactam hydrolysis in a one 'pot-procedure'. These imides were regioselectively reduced into corresponding N-acyliminium precursors, Which Subsequently submitted to an intramolecular aza-cyclization in acidic medium to provide novel 7-hexahydro-aza-indoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.072
• 作为产物：
  描述：

  2-溴-N-(2-苯乙基)乙酰胺 、 丙二腈 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到5-amino-2-oxo-1-(2-phenylethyl)-3H-pyrrole-4-carbonitrile
  参考文献：
  名称：

  Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams

  摘要：

  An effective route to novel polysubstituted imides is described, which involves the reaction of enamino-nitrile gamma-lactams derived from N-alkylated alpha-bromoacetamides and malononitrile with acryloyl chloride derivatives. This preceded via a sequence 1,4-addition-intramolecular peptidic coupling and a gamma-lactam hydrolysis in a one 'pot-procedure'. These imides were regioselectively reduced into corresponding N-acyliminium precursors, Which Subsequently submitted to an intramolecular aza-cyclization in acidic medium to provide novel 7-hexahydro-aza-indoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.072

文献信息

• Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams
  作者：Nabila Oukli、Sébastien Comesse、Nafa Chafi、Hassan Oulyadi、Adam Daïch

  DOI：10.1016/j.tetlet.2009.01.072

  日期：2009.4

  An effective route to novel polysubstituted imides is described, which involves the reaction of enamino-nitrile gamma-lactams derived from N-alkylated alpha-bromoacetamides and malononitrile with acryloyl chloride derivatives. This preceded via a sequence 1,4-addition-intramolecular peptidic coupling and a gamma-lactam hydrolysis in a one 'pot-procedure'. These imides were regioselectively reduced into corresponding N-acyliminium precursors, Which Subsequently submitted to an intramolecular aza-cyclization in acidic medium to provide novel 7-hexahydro-aza-indoles. (C) 2009 Elsevier Ltd. All rights reserved.