methyl (2S)-2-ethenyl-2-[(2S,5S)-2-methoxycarbonyl-5-prop-2-enylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate | 1096168-48-7

• 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: methyl (2S)-2-ethenyl-2-[(2S,5S)-2-methoxycarbonyl-5-prop-2-enylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 1096168-48-7
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: WBDQENHAMHTWIY-QWQRMKEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  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
• 作为产物：
  描述：

  (2S)-2-ethenyl-1-methoxycarbonylpyrrolidine-2-carboxylic acid 、 甲基(5S)-5-烯丙基-L-脯氨酸酯 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以36%的产率得到methyl (2S)-2-ethenyl-2-[(2S,5S)-2-methoxycarbonyl-5-prop-2-enylpyrrolidine-1-carbonyl]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