(2R,3R)-1,1-bis-[N-((1'R)-1'-phenyl-2'-hydroxyethyl)aminocarbonyl]-2,3-diphenylcyclopropane | 1256379-79-9

• 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: (2R,3R)-1,1-bis-[N-((1'R)-1'-phenyl-2'-hydroxyethyl)aminocarbonyl]-2,3-diphenylcyclopropane
• CAS: 1256379-79-9
• 化学式: C₃₃H₃₂N₂O₄
• 分子量: 520.628
• InChiKey: NHZUNONMWVQZPW-KRCBVYEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (2R,3R)-1,1-bis-[N-((1'R)-1'-phenyl-2'-hydroxyethyl)aminocarbonyl]-2,3-diphenylcyclopropane 在 甲基磺酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 2.0h， 以79%的产率得到(2R,3R)-1,1-di[(4'R)-4'-phenyloxazolin-2'-yl]-2,3-diphenylcyclopropane
  参考文献：
  名称：

  Novel C2-symmetric bisoxazolines with a chiral trans-(2R,3R)-diphenylcyclopropane backbone: preparation and application in several enantioselective catalytic reactions

  摘要：

  Various chiral bisoxazoline ligands with a chiral trans-(2R,3R)-diphenylcyclopropane backbone have been efficiently synthesized (five examples). These chiral ligands were tested and compared in palladium(0)catalysed enantioselective allylic alkylations (up to 97% ee), copper(I)-catalysed enantioselective cyclopropanations (up to 89% ee) and aziridinations (up to 90% ee). We observed that the presence of a stereogenic centre on the oxazoline moiety is mandatory in order to obtain acceptable enantioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.021
• 作为产物：
  描述：

  (2R,3R)-2,3-diphenylcyclopropane-1,1-dicarboxylic acid 、 D-苯甘氨醇 在 草酰氯 、 N,N-二甲基甲酰胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以80%的产率得到(2R,3R)-1,1-bis-[N-((1'R)-1'-phenyl-2'-hydroxyethyl)aminocarbonyl]-2,3-diphenylcyclopropane
  参考文献：
  名称：

  Novel C2-symmetric bisoxazolines with a chiral trans-(2R,3R)-diphenylcyclopropane backbone: preparation and application in several enantioselective catalytic reactions

  摘要：

  Various chiral bisoxazoline ligands with a chiral trans-(2R,3R)-diphenylcyclopropane backbone have been efficiently synthesized (five examples). These chiral ligands were tested and compared in palladium(0)catalysed enantioselective allylic alkylations (up to 97% ee), copper(I)-catalysed enantioselective cyclopropanations (up to 89% ee) and aziridinations (up to 90% ee). We observed that the presence of a stereogenic centre on the oxazoline moiety is mandatory in order to obtain acceptable enantioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.021