(2S)-N-[2-[[(2S)-pyrrolidine-2-carbonyl]amino]phenyl]-1-(2,4,6-trimethylphenyl)sulfonylpyrrolidine-2-carboxamide | 1430737-73-7

• 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: (2S)-N-[2-[[(2S)-pyrrolidine-2-carbonyl]amino]phenyl]-1-(2,4,6-trimethylphenyl)sulfonylpyrrolidine-2-carboxamide
• CAS: 1430737-73-7
• 化学式: C₂₅H₃₂N₄O₄S
• 分子量: 484.619
• InChiKey: FOVDFSUVZWABSB-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S)-1-(2,4,6-Trimethylbenzenesulfonyl)pyrrolidine-2-carboxylic acid 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2S)-N-[2-[[(2S)-pyrrolidine-2-carbonyl]amino]phenyl]-1-(2,4,6-trimethylphenyl)sulfonylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions

  摘要：

  An efficient, solvent-free protocol for the asymmetric aldol reaction between aldehydes and ketones using prolinamides 1-4 as organocatalysts is reported. Catalysts 2-4, in the presence of TFA (the ratio of catalyst and TFA = 1/1.5), proved to be excellent catalysts, giving the aldol products between aromatic aldehydes and ketones with nearly perfect diastereo- and enantioselectivities (up to >99:1 dr and >99% ee). This catalytic system can also be applied in the cross-aldol reaction of isatin with ketones and the Michael reaction between cyclohexane and nitroalkenes. A mechanism is proposed to account for the formation of the major enantiomer in this reaction. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.013

文献信息

• Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions
  作者：Furen Zhang、Chunmei Li、Chenze Qi

  DOI：10.1016/j.tetasy.2013.02.013

  日期：2013.4

  An efficient, solvent-free protocol for the asymmetric aldol reaction between aldehydes and ketones using prolinamides 1-4 as organocatalysts is reported. Catalysts 2-4, in the presence of TFA (the ratio of catalyst and TFA = 1/1.5), proved to be excellent catalysts, giving the aldol products between aromatic aldehydes and ketones with nearly perfect diastereo- and enantioselectivities (up to >99:1 dr and >99% ee). This catalytic system can also be applied in the cross-aldol reaction of isatin with ketones and the Michael reaction between cyclohexane and nitroalkenes. A mechanism is proposed to account for the formation of the major enantiomer in this reaction. (c) 2013 Elsevier Ltd. All rights reserved.