| 1097637-93-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• CAS: 1097637-93-8
• 化学式: C₄H₁₂N₂O₄*C₉H₁₀O₂
• 分子量: 302.327
• InChiKey: WHQHHQCJVDVVKL-QOXRBVBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  142.28
• 氢给体数：
  7.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2-苯基丙酸 、 (2S,3S)-2,3-dihydroxy-1,4-bis(hydroxyamino)butane 以 乙醇 、 异丙醇 为溶剂， 生成 、
  参考文献：
  名称：

  Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy- and (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butanes

  摘要：

  Two enantiopure bis(hydroxyamino) compounds were Successfully prepared from dialkyl tartrate by a chiral-pool method and applied as basic resolving agents in the enantioseparation of 2-arylpropanoic acids and arylglycolic acids. (2S,3S)-2,3-Dihydroxy-1,4-bis(hydroxyamino)butane (2S,3S)-1a could moderately recognize the chirality of the 2-arylpropanoic acids, while (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butane (2S,3S)-1b could not due to the low crystallinity of both the corresponding diastereomeric salts. On the other hand, (2S,3S)-1b showed a similar chirality-recognition ability for the arylglycolic acids. The ability of (2S,3S)-1b was different from those generally observed for widely used primary amine-type resolving agents with regard to the relationship between the resolution efficiency and the similarity in the relative molecular length of a resolving agent and a target racemate. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that in the salts (2S,3S)-1a formed a supramolecular sheet, of which the distance was variable to make the resultant dissymmetric space fit to the shape of the target acids, and that (2S,3S)-1b was constructed from a robust supramolecular sheet, consisting of hydrogen-bonding 21 columns, with the participation of the hydroxy group of the arylglycolic acids. These X-ray crystallographic analyses also suggested that for the formation of a supramolecular sheet, the coexistence of two hydroxyamino groups is essential. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.006