dimethyl (3S,6S,9aS)-5-oxospiro[2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-6,2'-pyrrolidine]-1',3-dicarboxylate | 1096168-50-1

• 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: dimethyl (3S,6S,9aS)-5-oxospiro[2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-6,2'-pyrrolidine]-1',3-dicarboxylate
• CAS: 1096168-50-1
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: WAQNAZGVALAYMV-BFQNTYOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (3S,6S,9aS)-5-oxospiro[2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-6,2'-pyrrolidine]-1',3-dicarboxylate 、 甲胺 以 乙醇 为溶剂， 以91%的产率得到methyl (3S,6S,9aS)-3-(methylcarbamoyl)-5-oxospiro[2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-6,2'-pyrrolidine]-1'-carboxylate
  参考文献：
  名称：

  A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic

  摘要：

  A new proline-based spirotricyclic lactam is reported as an efficient type II' beta-turn inducing peptidomimetic. After investigations of the reverse turn properties by Computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction Of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged Structure to be employed as a mimic of the beta-turn motif of the potent antibiotic Gramicidin S. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.072
• 作为产物：
  描述：

  methyl (2S)-2-ethenyl-2-[(2S,5S)-2-methoxycarbonyl-5-prop-2-enylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以76%的产率得到dimethyl (3S,6S,9aS)-5-oxospiro[2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]azepine-6,2'-pyrrolidine]-1',3-dicarboxylate
  参考文献：
  名称：

  A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic

  摘要：

  A new proline-based spirotricyclic lactam is reported as an efficient type II' beta-turn inducing peptidomimetic. After investigations of the reverse turn properties by Computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction Of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged Structure to be employed as a mimic of the beta-turn motif of the potent antibiotic Gramicidin S. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.072