(S)-N-((2S,3R)-1-hydroxy-3-methyl-1,1-diphenylpentan-2-yl)azetidine-2-carboxamide | 1551161-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-((2S,3R)-1-hydroxy-3-methyl-1,1-diphenylpentan-2-yl)azetidine-2-carboxamide
• 英文别名: (2S)-N-[(2S,3R)-1-hydroxy-3-methyl-1,1-diphenylpentan-2-yl]azetidine-2-carboxamide
• CAS: 1551161-34-2
• 化学式: C₂₂H₂₈N₂O₂
• 分子量: 352.477
• InChiKey: VMLYMRYKPSZKKU-UXPWSPDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-N-((2S,3R)-1-hydroxy-3-methyl-1,1-diphenylpentan-2-yl)-1-tritylazetidine-2-carboxamide 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以76%的产率得到(S)-N-((2S,3R)-1-hydroxy-3-methyl-1,1-diphenylpentan-2-yl)azetidine-2-carboxamide
  参考文献：
  名称：

  Enantiopure azetidine-2-carboxamides as organocatalysts for direct asymmetric aldol reactions in aqueous and organic media

  摘要：

  A family of enantiopure azetidine-2-caboxamides was asymmetrically synthesized, and was examined as organocatalyst in direct aldol reactions. A well chosen chiral azetidine-2-caboxamide was found to smoothly catalyze the direct aldol reaction of various benzaldehydes with acetone in brine, and beta-hydroxy ketones were produced with enantiomeric excess up to 96%. The reaction of benzaldehydes with cyclic ketones also led to the formation of anti-products in diastereomeric ratio up to 99:1 and enantiomeric excess up to 99%. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.081

文献信息

• Enantiopure azetidine-2-carboxamides as organocatalysts for direct asymmetric aldol reactions in aqueous and organic media
  作者：Xixi Song、Ai-Xiang Liu、Shan-Shan Liu、Wen-Chao Gao、Min-Can Wang、Junbiao Chang

  DOI：10.1016/j.tet.2013.12.081

  日期：2014.2

  A family of enantiopure azetidine-2-caboxamides was asymmetrically synthesized, and was examined as organocatalyst in direct aldol reactions. A well chosen chiral azetidine-2-caboxamide was found to smoothly catalyze the direct aldol reaction of various benzaldehydes with acetone in brine, and beta-hydroxy ketones were produced with enantiomeric excess up to 96%. The reaction of benzaldehydes with cyclic ketones also led to the formation of anti-products in diastereomeric ratio up to 99:1 and enantiomeric excess up to 99%. (c) 2014 Elsevier Ltd. All rights reserved.