(1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-chloro-1-phenyl-ethyl)-amide] | 198224-00-9

• 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: (1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-chloro-1-phenyl-ethyl)-amide]
• CAS: 198224-00-9
• 化学式: C₂₅H₂₆Cl₂N₂O₂
• 分子量: 457.4
• InChiKey: ZIUWZCCXWULOKP-YPEXMJEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-chloro-1-phenyl-ethyl)-amide] 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以31%的产率得到(4S)-4-phenyl-2-[(1S,2R,3R,4R)-3-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-2-bicyclo[2.2.1]hept-5-enyl]-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6
• 作为产物：
  描述：

  (1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (1S,2R,3R,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-chloro-1-phenyl-ethyl)-amide]
  参考文献：
  名称：

  Enantioselective Diels-Alder reactions: novel constrained bis(oxazoline) ligand-metal triflate catalysts

  摘要：

  Five chiral 1,4-bis(oxazoline) ligands, each bearing a bicyclic backbone, were prepared and examined in Mg(OTf)(2)-, Zn(OTf)(2)-, and Cu(OTf)(2)-catalyzed Diels-Alder reactions. The cycloadditions were carried out at room temperature and afforded enantiomeric excess up to 88%. Surprisingly, a non-C-2-symmetric bis(oxazoline) bearing a meso backbone was among the more efficient ligands examined. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00323-6