(1S,2S)-1-benzyl-N-(2-hydroxy-1-phenylethyl)-2-methylazetidine-2-carboxamide | 1384745-34-9

• 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: (1S,2S)-1-benzyl-N-(2-hydroxy-1-phenylethyl)-2-methylazetidine-2-carboxamide
• 英文别名: (2S)-1-benzyl-N-[(1S)-2-hydroxy-1-phenylethyl]-2-methylazetidine-2-carboxamide
• CAS: 1384745-34-9
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: LCPXZGOIUKHUDZ-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-benzyl-N-(2-hydroxy-1-phenylethyl)-2-methylazetidine-2-carboxamide 在 硫酸 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 64.0h， 生成 (S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

  摘要：

  A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.006
• 作为产物：
  描述：

  Tert-butyl 1-benzyl-2-methylazetidine-2-carboxylate 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,2S)-1-benzyl-N-(2-hydroxy-1-phenylethyl)-2-methylazetidine-2-carboxamide
  参考文献：
  名称：

  Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

  摘要：

  A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.006