ethyl 3-(1-ethoxycarbonyl-1-phenyl)methylamino-2-hydroxy-3-phenylpropionate

• 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: ethyl 3-(1-ethoxycarbonyl-1-phenyl)methylamino-2-hydroxy-3-phenylpropionate
• 英文别名: ethyl (2R,3R)-3-[(2-ethoxy-2-oxo-1-phenylethyl)amino]-2-hydroxy-3-phenylpropanoate
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: YPZFFRNKGUFMEL-ZYYFHIKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-(1-ethoxycarbonyl-1-phenyl)methylamino-2-hydroxy-3-phenylpropionate 、 溴甲苯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以63%的产率得到ethyl 3-[N-benzyl-N-[(1-ethoxycarbonyl-1-phenyl)methyl]amino]-2-hydroxy-3-phenylpropionate
  参考文献：
  名称：

  Practical Preparation of β‐Amino‐α‐Hydroxy Diesters: Key Intermediates for 1,4‐Oxazin‐2‐Ones

  摘要：

  In the presence of a catalytic amount of amino acid hydrochloride, trans-beta-phenylglycidic ester undergoes ring opening with high stereo- and regioselectivity when treated with glycine esters. Alkylation of the resulting beta-amino-alpha-hydroxy diesters with benzyl bromide, followed by cyclization to furnish the expected 1,4-oxazin-2-ones, is also described.

  DOI：

  10.1080/00397910701574965
• 作为产物：
  描述：

  2-氨基-2-苯乙酸乙酯 、 反式-3-苯基环氧丙酸乙酯 在 NH₂CH(C₆H₅)-CO₂Et hydrochloride 作用下， 以 乙醇 为溶剂， 反应 40.0h， 以87%的产率得到ethyl 3-(1-ethoxycarbonyl-1-phenyl)methylamino-2-hydroxy-3-phenylpropionate
  参考文献：
  名称：

  Practical Preparation of β‐Amino‐α‐Hydroxy Diesters: Key Intermediates for 1,4‐Oxazin‐2‐Ones

  摘要：

  In the presence of a catalytic amount of amino acid hydrochloride, trans-beta-phenylglycidic ester undergoes ring opening with high stereo- and regioselectivity when treated with glycine esters. Alkylation of the resulting beta-amino-alpha-hydroxy diesters with benzyl bromide, followed by cyclization to furnish the expected 1,4-oxazin-2-ones, is also described.

  DOI：

  10.1080/00397910701574965

文献信息

• Practical Preparation of β‐Amino‐α‐Hydroxy Diesters: Key Intermediates for 1,4‐Oxazin‐2‐Ones
  作者：Brahim Ould Elemine、Rafâa Besbes、Mohamed Rached Ennigrou

  DOI：10.1080/00397910701574965

  日期：2007.11

  In the presence of a catalytic amount of amino acid hydrochloride, trans-beta-phenylglycidic ester undergoes ring opening with high stereo- and regioselectivity when treated with glycine esters. Alkylation of the resulting beta-amino-alpha-hydroxy diesters with benzyl bromide, followed by cyclization to furnish the expected 1,4-oxazin-2-ones, is also described.