(S)-2-(t-butoxycarbonylamino)-3-methyl-N-methyl-N-(1,2-propadienyl)butanamide | 1133721-57-9

• 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)-3-methyl-N-methyl-N-(1,2-propadienyl)butanamide
• CAS: 1133721-57-9
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: GYYMDBZRTKWYFQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(t-butoxycarbonylamino)-3-methyl-N-methyl-N-(1,2-propadienyl)butanamide 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以10%的产率得到C₁₂H₂₂N₂O₄
  参考文献：
  名称：

  Gold-catalyzed intramolecular hydroamination of α-amino allenamides as a route to enantiopure 2-vinylimidazolidinones

  摘要：

  An efficient gold-catalyzed procedure for the preparation of 2-vinylimidazolidinones has been developed. The starting materials for the synthesis of these compounds are alpha-amino allenamides which undergo heterocyclization by means of nucleophilic attack of the amino group on the inside double bond of the 1,2-diene moiety. This is the first example of a gold-catalyzed cyclization on allene substrates bearing an amido group which, however, resulted inactive. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.011
• 作为产物：
  描述：

  (S)-2-(t-butoxycarbonylamino)-3-methyl-N-methyl-N-propargylbutanamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以98%的产率得到(S)-2-(t-butoxycarbonylamino)-3-methyl-N-methyl-N-(1,2-propadienyl)butanamide
  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

文献信息

• Access to a Novel Class of Tetracyclic 1,4-Benzodiazepin-5-ones Starting from α-Amino Acids by Pd-Catalyzed Amination/1,3-Dipolar Cycloaddition as the Key Steps
  作者：Luca Basolo、Egle M. Beccalli、Elena Borsini、Gianluigi Broggini、Maisaa Khansaa、Micol Rigamonti

  DOI：10.1002/ejoc.200901290

  日期：2010.3

  preparation of the novel class of tetracyclic imidazo[2,1-c]pyrazolo[1,5-a][1,4]benzodiazepine-5,8-diones is reported. The protocol uses cheap and easily accessible α-amino acids as chiral-pool starting materials and leads to products in an enantiopure form. An intramolecular palladium-catalyzed amination process to form the imidazole nucleus and an intramolecular 1,3-dipolar cycloaddition reaction to simultaneously

  报道了一种用于制备新型四环咪唑并 [2,1-c] 吡唑并 [1,5-a][1,4] 苯并二氮杂-5,8-二酮类的简便方法。该协议使用廉价且易于获取的 α-氨基酸作为手性池起始材料，并产生对映纯形式的产品。分子内钯催化胺化过程形成咪唑核和分子内1,3-偶极环加成反应同时获得吡唑和1,4-二氮杂环是关键步骤。
• 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.