(S)-tert-butyl 2-{3-[(1S,2S)-2-amino-1,2-diphenylethyl]thioureido}-3-phenylpropanoate | 1198297-74-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-tert-butyl 2-{3-[(1S,2S)-2-amino-1,2-diphenylethyl]thioureido}-3-phenylpropanoate
• CAS: 1198297-74-3
• 化学式: C₂₈H₃₃N₃O₂S
• 分子量: 475.655
• InChiKey: FERZSERAEXBUTN-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.38
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl 2-isothiocyanato-3-phenylpropanoate 、 (1S,2S)-1,2-二苯基乙二胺 以 二氯甲烷 为溶剂， 生成 (S)-tert-butyl 2-{3-[(1S,2S)-2-amino-1,2-diphenylethyl]thioureido}-3-phenylpropanoate
  参考文献：
  名称：

  基于天然氨基酸叔丁基酯的伯胺-硫脲作为迈克尔反应的有机催化剂

  摘要：

  Abstractmagnified imageA new class of primary amine‐thioureas based on tert‐butyl esters of (S)‐α‐amino acids and (1S,2S)‐diphenylethylenediamine was synthesized and their activity as catalysts in Michael additions was evaluated. Derivatives based on di‐tert‐butyl aspartate and tert‐butyl O‐tert‐butyl threoninate provided the product of the reaction between trans‐β‐nitrostyrene and acetone in quantitative yield and high enantioselectivity (87–91% ee). All the thioureas based on tert‐butyl esters of amino acids catalyzed the reaction of nitroolefins with acetophenone with high enantioselectivity (92–98% ee). Thus, low‐cost, commercially available tert‐butyl esters of natural amino acids are very important chiral building blocks for the construction of novel chiral thioureas able to catalyze asymmetric Michael additions with high enantioselectivity.

  DOI：

  10.1002/adsc.200800812