1-(tert-butyl)-3-(((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea | 1353716-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 1-(tert-butyl)-3-(((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea
• CAS: 1353716-30-9
• 化学式: C₁₅H₂₇N₃O
• 分子量: 265.399
• InChiKey: XXUPBKZARJGEOQ-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.37
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-[(2S,4S,5R)-5-乙烯基-1-氮杂双环[2.2.2]辛-2-基]甲胺 、 叔丁基异氰酸酯 在 二月桂酸二丁基锡 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以55%的产率得到1-(tert-butyl)-3-(((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea
  参考文献：
  名称：

  Molecular Recognition Principles and Stationary-Phase Characteristics of Topoisomer-Selective Chemoaffinity Materials for Chromatographic Separation of Circular Plasmid DNA Topoisomers

  摘要：

  We recently discovered the molecular recognition capability of a quinine carbamate ligand attached to silica as a powerful chemoaffinity material for the chromatographic separation of circular plasmid topoisomers of different linking numbers. In this paper we develop structure selectivity relationship studies to figure out the essential structural features for topoisomer recognition. By varying different moieties of the original cinchonan-derived selector, it was shown that intercalation by the quinoline moiety of the ligand as assumed initially as the working hypothesis is not an essential feature for topoisomer recognition during chromatography. We found that the key elements for topoisomer selectivity are the presence of a rigid weak anion-exchange site and a H-donor site separated from each other in a defined distance by a 4-atom spacer. Additionally, incorporation of the weak anion-exchange site into a cyclic ring structure provides greater rigidity of the ligand molecule and turned out to be advantageous, if not mandatory, for (close to) baseline separation.

  DOI：

  10.1021/ja210241a