ethyl (2S,1'R)-2-chloro-3-[2-methoxy-2-oxo-N-(1'-phenylethyl)acetamido]propionate | 910655-44-6

• 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 (2S,1'R)-2-chloro-3-[2-methoxy-2-oxo-N-(1'-phenylethyl)acetamido]propionate
• CAS: 910655-44-6
• 化学式: C₁₆H₂₀ClNO₅
• 分子量: 341.791
• InChiKey: YCGWGKWWHKWKPB-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (2S,1'R)-2-chloro-3-[2-methoxy-2-oxo-N-(1'-phenylethyl)acetamido]propionate 在 silver(I) acetate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到(6R,1'R)-6-ethoxycarbonyl-4-(1'-phenylethyl)morpholine-2,3-dione
  参考文献：
  名称：

  Ring opening of 2-acylaziridines by acid chlorides

  摘要：

  Good nucleophilicity of the ring nitrogen in chiral (2R,1'R)-2-acyl-(1'-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the beta-amino-alpha-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, beta-amino-alpha-acetyloxypropionates, and morpholin-2,3-diones, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.025
• 作为产物：
  描述：

  甲基戊酰氯 、 ethyl (2R)-1-[(1R)-1-phenylethyl]-aziridine-2-carboxylate 以 乙腈 为溶剂， 反应 1.0h， 以89%的产率得到ethyl (2S,1'R)-2-chloro-3-[2-methoxy-2-oxo-N-(1'-phenylethyl)acetamido]propionate
  参考文献：
  名称：

  Ring opening of 2-acylaziridines by acid chlorides

  摘要：

  Good nucleophilicity of the ring nitrogen in chiral (2R,1'R)-2-acyl-(1'-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the beta-amino-alpha-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, beta-amino-alpha-acetyloxypropionates, and morpholin-2,3-diones, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.025