(2S)-N-[(S)-1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide hydrochloride | 1126529-54-1

• 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: (2S)-N-[(S)-1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide hydrochloride
• CAS: 1126529-54-1
• 化学式: C₂₁H₂₅N₃O₄S*ClH
• 分子量: 451.974
• InChiKey: KTNRFWOATKLAQB-HLRBRJAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104.37
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  tert-butyl (2S)-2-[(S)-1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-ylcarbamoyl]pyrrolidine-1-carboxylate 在 盐酸 、 甲醇 作用下， 反应 1.0h， 以93%的产率得到(2S)-N-[(S)-1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide hydrochloride
  参考文献：
  名称：

  Sulfonamides of homoproline and dipeptides as organocatalysts for Michael and aldol reactions

  摘要：

  Sulfonamides of the non-natural amino acid homoproline and the dipeptide Pro-Phe were synthesised and evaluated for their catalytic activity in Michael and aldol reactions. Sulfonamides of homoproline outperform proline and Pro-Phe in the Michael reaction, whereas sulfonamides of Pro-Phe lead to better results in the aldol reaction. The results of the present study show that the conversion of the carboxylic group of either homoproline or dipeptide Pro-Phe to the bioisosteric acyl sulfonamide group lead to improved organocatalysts. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.008