(4R,5R)-(+)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate | 135075-62-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5R)-(+)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate
• 英文别名: methyl (E)-3-[(4R,5R)-1,3,4,5-tetraphenylimidazolidin-2-yl]prop-2-enoate
• CAS: 135075-62-6
• 化学式: C₃₁H₂₈N₂O₂
• 分子量: 460.576
• InChiKey: BCVOFBJVDBROEB-QBYLACLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-(+)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate 在 正丁基锂 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028
• 作为产物：
  描述：

  富马醛酸甲酯 、 rac-1,2-dianilino-1,2-diphenylethane 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 以88%的产率得到(4R,5R)-(+)-(E)-3-(1,3,4,5-Tetraphenylimidazolidin-2-yl)propenoate
  参考文献：
  名称：

  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-.alpha.,.beta.-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller

  摘要：

  The 1,3-dipolar cycloaddition of N-metalated azomethine ylides to chiral (E)-3-(1,3-disubstituted 4,5-diphenylimidazolidin-2-yl)propenoates proceeded highly diastereoselectively. The previously unknown absolute configuration of optically pure 1,2-dianilino-1,2-diphenylethane was determined from the absolute configuration of the cycloadducts. What diastereotopic olefin face of the alpha,beta-unsaturated ester was attacked by the ylide was found to depend dramatically upon the nature of N substituents of the chiral controller as well as upon the bulkiness of the ester moiety of the ylide.

  DOI：

  10.1021/jo00014a028