ethyl (E)-3-acetamido-2-pentenoate | 448222-31-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3-acetamido-2-pentenoate
• 英文别名: ethyl (E)-3-acetamidopent-2-enoate
• CAS: 448222-31-9
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: YPRACKKCYLLTDI-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-acetamido-2-pentenoate 在 [Rh((S,S)-Me-BDPMI)(COD))BF₄] 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.36 kPa 条件下， 反应 12.0h， 生成 (S)-(-)-Beta-N-乙酰基-丝氨酸乙酯 、 ethyl (R)-3-acetamidopentanoate
  参考文献：
  名称：

  Rh(I)-Catalyzed Enantioselective Hydrogenation of (E)- and (Z)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions

  摘要：

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.

  DOI：

  10.1021/ol0261884
• 作为产物：
  描述：

  丙酰乙酸乙酯 在 吡啶 、 ammonium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 72.0h， 生成 ethyl (E)-3-acetamido-2-pentenoate
  参考文献：
  名称：

  Rh(I)-Catalyzed Enantioselective Hydrogenation of (E)- and (Z)-β-(Acylamino)acrylates Using 1,4-Bisphosphine Ligands under Mild Conditions

  摘要：

  [GRAPHICS]Rh-Me-BDPMI (1a) complex can be an effective catalyst for the hydrogenations of (E)- and (2)-beta-(acylamino)acrylates, in which the Zisomers hydrogenated with the same or even higher ee values than the corresponding E-isomers. The conversion yield and enantioselectivity of E-and Z-isomers were largely dependent on the solvent, and thus, the E-isomers were hydrogenated more effectively in CH2Cl2, whereas the Z-isomers were hydrogenated more effectively in polar MeOH solvent.

  DOI：

  10.1021/ol0261884