ethyl (Z)-2-(methoxycarbonylamino)-4-phenylbut-2-enoate | 288068-74-6

• 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 (Z)-2-(methoxycarbonylamino)-4-phenylbut-2-enoate
• CAS: 288068-74-6
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: FKDYOJSXMFIPOU-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-2-(methoxycarbonylamino)-4-phenylbut-2-enoate 在 [Rh(S-1)(COD)]BF₄ 盐酸 、 氢气 作用下， 以 丙酮 、 甲苯 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 7.0h， 生成 (S)-2-<(Methoxycarbonyl)amino>-4-phenylbutanoic Acid
  参考文献：
  名称：

  An efficient synthesis of chiral homophenylalanine derivatives via enantioselective hydrogenation

  摘要：

  Chiral homophenylalanine derivatives were synthesized via enantioselective hydrogenation of 5a and 5b catalyzed by rhodium complexes bearing chiral phosphine and phosphinite legands. Enantiomeric excesses up to 96.2% were achieved when S-spiroOP(S-1) was used as a chiral ligand under 500 psi of H-2 pressure in acetone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00424-3
• 作为产物：
  描述：

  Phenethylmagnesium chloride 以 乙醚 为溶剂， 生成 ethyl (Z)-2-(methoxycarbonylamino)-4-phenylbut-2-enoate
  参考文献：
  名称：

  An efficient synthesis of chiral homophenylalanine derivatives via enantioselective hydrogenation

  摘要：

  Chiral homophenylalanine derivatives were synthesized via enantioselective hydrogenation of 5a and 5b catalyzed by rhodium complexes bearing chiral phosphine and phosphinite legands. Enantiomeric excesses up to 96.2% were achieved when S-spiroOP(S-1) was used as a chiral ligand under 500 psi of H-2 pressure in acetone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00424-3

文献信息

• DPAMPP in catalytic asymmetric reactions: enantioselective synthesis of l- homophenylalanine
  作者：Yinong Xie、Rongliang Lou、Zhi Li、Aiqiao Mi、Yaozhong Jiang

  DOI：10.1016/s0957-4166(00)00092-6

  日期：2000.4

  L-Homophenylalanine 1, a key intermediate of most commercially important ACE inhibitors, was prepared via catalytic asymmetric hydrogenation of (Z)-2-acetamido-4-phenylcrotonate 3a with a cationic rhodium complex of(1 R,2S)-DPAMPP, followed by acid-hydrolysis of the protecting groups in good yield with >99.9% enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.