1-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-N,N-dimethylcyclopentanecarboxamide | 266338-66-3

• 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: 1-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-N,N-dimethylcyclopentanecarboxamide
• 英文别名: 1-[(3-hydroxy-2-phenylpropanoyl)amino]-N,N-dimethylcyclopentane-1-carboxamide
• CAS: 266338-66-3
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: PXKIBOIOHSHYSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-N,N-dimethylcyclopentanecarboxamide 在 盐酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 49.0h， 生成 1-{1-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]cyclopentanecarboxamido}-N,N-dimethylcyclopentanecarboxamide
  参考文献：
  名称：

  Synthesis of 16-Membered Cyclic Depsipeptidesvia Direct Amide Cyclization

  摘要：

  The 2,2-disubstituted 2H-azirin-3-amines 5 (3-amino-2H-azirines) were used as synthons for alpha,alpha-disubstituted a-amino acids in the preparation of 16-membered cyclic depsipeptides 13. The linear precursors containing four alpha,alpha-disubstituted alpha-amino acids, the pentapeptides 12, were synthesized from beta-hydroxy acids 4 via the 'azirine/oxazolone method' (Scheme 2). The 16-membered cyclic depsipeptides 13 were prepared via 'direct amide cyclization' in good-to-excellent yields (Schemes 3 and 4). In addition to the desired cyclic monomer 13, which was obtained as the main product, the cyclodimer 14 could also be isolated. The cyclization conditions were investigated and found to be optimum with HCl in toluene at 100 degrees. The structure and conformation of the cyclic depsipeptide 13b was established by X-ray crystallography.

  DOI：

  10.1002/(sici)1522-2675(20000119)83:1<233::aid-hlca233>3.0.co;2-1
• 作为产物：
  描述：

  DL-托品酸 、 N,N-dimethyl-1-azaspiro[2.4]hept-1-en-2-amine 以 乙腈 为溶剂， 反应 48.0h， 以93%的产率得到1-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-N,N-dimethylcyclopentanecarboxamide
  参考文献：
  名称：

  Synthesis of 16-Membered Cyclic Depsipeptidesvia Direct Amide Cyclization

  摘要：

  The 2,2-disubstituted 2H-azirin-3-amines 5 (3-amino-2H-azirines) were used as synthons for alpha,alpha-disubstituted a-amino acids in the preparation of 16-membered cyclic depsipeptides 13. The linear precursors containing four alpha,alpha-disubstituted alpha-amino acids, the pentapeptides 12, were synthesized from beta-hydroxy acids 4 via the 'azirine/oxazolone method' (Scheme 2). The 16-membered cyclic depsipeptides 13 were prepared via 'direct amide cyclization' in good-to-excellent yields (Schemes 3 and 4). In addition to the desired cyclic monomer 13, which was obtained as the main product, the cyclodimer 14 could also be isolated. The cyclization conditions were investigated and found to be optimum with HCl in toluene at 100 degrees. The structure and conformation of the cyclic depsipeptide 13b was established by X-ray crystallography.

  DOI：

  10.1002/(sici)1522-2675(20000119)83:1<233::aid-hlca233>3.0.co;2-1

文献信息

• Synthesis of 16-Membered Cyclic Depsipeptidesvia Direct Amide Cyclization
  作者：Kristian N. Koch、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(20000119)83:1<233::aid-hlca233>3.0.co;2-1

  日期：2000.1.19

  The 2,2-disubstituted 2H-azirin-3-amines 5 (3-amino-2H-azirines) were used as synthons for alpha,alpha-disubstituted a-amino acids in the preparation of 16-membered cyclic depsipeptides 13. The linear precursors containing four alpha,alpha-disubstituted alpha-amino acids, the pentapeptides 12, were synthesized from beta-hydroxy acids 4 via the 'azirine/oxazolone method' (Scheme 2). The 16-membered cyclic depsipeptides 13 were prepared via 'direct amide cyclization' in good-to-excellent yields (Schemes 3 and 4). In addition to the desired cyclic monomer 13, which was obtained as the main product, the cyclodimer 14 could also be isolated. The cyclization conditions were investigated and found to be optimum with HCl in toluene at 100 degrees. The structure and conformation of the cyclic depsipeptide 13b was established by X-ray crystallography.