(4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate | 749253-94-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate
• CAS: 749253-94-9
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: IAQGHYHUWCXXPW-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以76%的产率得到(4S,5S)-(+)-4-(hydroxymethyl)-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  Asymmetric Synthesis of syn-(2R,3S)- and anti-(2S,3S)-Ethyl Diamino-3-phenylpropanoates from N-(Benzylidene)-p-toluenesulfinamide and Glycine Enolates

  摘要：

  Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.

  DOI：

  10.1021/ol048981y
• 作为产物：
  描述：

  (2S,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate 在 N,N'-羰基二咪唑 作用下， 生成 (4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate
  参考文献：
  名称：

  Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates

  摘要：

  Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.001