(1R,2S)-N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-3,3-dimethyl-1,2-cyclopropanedicarboxamide | 1394965-75-3

• 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: (1R,2S)-N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-3,3-dimethyl-1,2-cyclopropanedicarboxamide
• CAS: 1394965-75-3
• 化学式: C₂₃H₂₈N₂O₄
• 分子量: 396.486
• InChiKey: DNHVTGGQLDMTEX-LWYYNNOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.66
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-3,3-dimethyl-1,2-cyclopropanedicarboxamide 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以53%的产率得到(1R,2S)-1,2-bis[4(R)-phenyloxazolin-2-yl]-3,3-dimethylcyclopropane
  参考文献：
  名称：

  Catalytic asymmetric nitroaldol (Henry) reactions with copper(II)/cyclopropane-based bisoxazoline complexes

  摘要：

  A series of cyclopropane-based bisoxazolines were synthesized from (R)- and (S)-amino alcohols, and applied to copper-catalyzed enantioselective nitroaldol reactions between nitromethane and various aldehydes. The reactions generated beta-hydroxy nitroalkanes in high yields (97%) and with good enantioselectivities (up to 87% ee). The effects of the oxazoline stereocenters constructed in the Henry reactions were also studied. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.014
• 作为产物：
  描述：

  D-苯甘氨醇 、 (1R,2S)-3,3-二甲基-1,2-环丙烷二羰基二氯化物 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以45%的产率得到(1R,2S)-N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]-3,3-dimethyl-1,2-cyclopropanedicarboxamide
  参考文献：
  名称：

  Catalytic asymmetric nitroaldol (Henry) reactions with copper(II)/cyclopropane-based bisoxazoline complexes

  摘要：

  A series of cyclopropane-based bisoxazolines were synthesized from (R)- and (S)-amino alcohols, and applied to copper-catalyzed enantioselective nitroaldol reactions between nitromethane and various aldehydes. The reactions generated beta-hydroxy nitroalkanes in high yields (97%) and with good enantioselectivities (up to 87% ee). The effects of the oxazoline stereocenters constructed in the Henry reactions were also studied. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.014