(S)-2-(t-butoxycarbonylamino)-N-methyl-2-phenyl-N-propargylacetamide | 1133721-55-7

• 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: (S)-2-(t-butoxycarbonylamino)-N-methyl-2-phenyl-N-propargylacetamide
• 英文别名: tert-butyl N-[(1S)-2-[methyl(prop-2-ynyl)amino]-2-oxo-1-phenylethyl]carbamate
• CAS: 1133721-55-7
• 化学式: C₁₇H₂₂N₂O₃
• 分子量: 302.373
• InChiKey: CXNWWHBZVLTYQI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(t-butoxycarbonylamino)-N-methyl-2-phenyl-N-propargylacetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以95%的产率得到(S)-2-(t-butoxycarbonylamino)-N-methyl-2-phenyl-N-(1,2-propadienyl)acetamide
  参考文献：
  名称：

  Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of l-α-aminoacids

  摘要：

  Allenylamides of Boc-protected alpha-aminoacids easily gave in basic medium heterocyclic products arising from attack of the NH group on the inside C-C double bond of the 1,2-diene moiety, namely imidazolidinones, pyrazinones, and a pyrrole compound. The microwave-assisted heterocyclization occurred cleanly at C-beta of the allenyl group with formation of pyrazin-2-ones having an endo- or exocyclic double bond. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.074
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 N-(叔丁氧羰基)-L-2-苯甘氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到(S)-2-(t-butoxycarbonylamino)-N-methyl-2-phenyl-N-propargylacetamide
  参考文献：
  名称：

  Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones

  摘要：

  Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.

  DOI：

  10.1021/ol900171g

文献信息

• Palladium-Catalyzed Domino Carbopalladation/5-<i>exo</i>-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones
  作者：Egle M. Beccalli、Gianluigi Broggini、Francesca Clerici、Simona Galli、Claire Kammerer、Micol Rigamonti、Silvia Sottocornola

  DOI：10.1021/ol900171g

  日期：2009.4.2

  Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.
• Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of l-α-aminoacids
  作者：Gianluigi Broggini、Simona Galli、Micol Rigamonti、Silvia Sottocornola、Gaetano Zecchi

  DOI：10.1016/j.tetlet.2009.01.074

  日期：2009.4

  Allenylamides of Boc-protected alpha-aminoacids easily gave in basic medium heterocyclic products arising from attack of the NH group on the inside C-C double bond of the 1,2-diene moiety, namely imidazolidinones, pyrazinones, and a pyrrole compound. The microwave-assisted heterocyclization occurred cleanly at C-beta of the allenyl group with formation of pyrazin-2-ones having an endo- or exocyclic double bond. (C) 2009 Elsevier Ltd. All rights reserved.