tert-butyl (2S)-2-[(6R,8aR)-8a-carbamoyl-5-oxospiro[2,3,7,8-tetrahydro-1H-indolizine-6,2'-pyrrolidine]-1'-carbonyl]pyrrolidine-1-carboxylate | 881032-79-7

• 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: tert-butyl (2S)-2-[(6R,8aR)-8a-carbamoyl-5-oxospiro[2,3,7,8-tetrahydro-1H-indolizine-6,2'-pyrrolidine]-1'-carbonyl]pyrrolidine-1-carboxylate
• CAS: 881032-79-7
• 化学式: C₂₂H₃₄N₄O₅
• 分子量: 434.536
• InChiKey: ISOLFZCCBTZNPL-ITEAAPOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(6R,8aR)-8a-carbamoyl-5-oxospiro[2,3,7,8-tetrahydro-1H-indolizine-6,2'-pyrrolidine]-1'-carbonyl]pyrrolidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.42h， 以66%的产率得到(6R,8aR)-5-oxo-1'-[(2S)-pyrrolidine-2-carbonyl]spiro[2,3,7,8-tetrahydro-1H-indolizine-6,2'-pyrrolidine]-8a-carboxamide;hydrochloride
  参考文献：
  名称：

  Concerted Synthesis of a Spirobicyclic Type-VI β-Turn Mimic of Pro-Pro-Pro-NH₂

  摘要：

  A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i + 1 and i + 2 residues are identical.

  DOI：

  10.1021/ol0600335
• 作为产物：
  描述：

  (2R,2'R)-2,2'-ethano-cyclo(Pro-Pro) 在 N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 2-氯-1-甲基吡啶碘化物 、 氨 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 tert-butyl (2S)-2-[(6R,8aR)-8a-carbamoyl-5-oxospiro[2,3,7,8-tetrahydro-1H-indolizine-6,2'-pyrrolidine]-1'-carbonyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Concerted Synthesis of a Spirobicyclic Type-VI β-Turn Mimic of Pro-Pro-Pro-NH₂

  摘要：

  A highly concerted strategy for the synthesis of symmetrical type-VI beta-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI beta-turn mimics where the i + 1 and i + 2 residues are identical.

  DOI：

  10.1021/ol0600335