2-乙酰氨基-3-(4-氟苯基)-2-甲氧基丙酸甲酯 | 1262841-26-8

• 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
• 中文名称: 2-乙酰氨基-3-(4-氟苯基)-2-甲氧基丙酸甲酯
• 英文名称: methyl 2-acetamido-3-(4-fluorophenyl)-2-methoxypropanoate
• CAS: 1262841-26-8
• 化学式: C₁₃H₁₆FNO₄
• 分子量: 269.273
• InChiKey: VGQUDTJPAKQNAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-3-(4-氟苯基)-2-甲氧基丙酸甲酯 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以75%的产率得到甲基N-乙酰基-4-氟苯丙氨酸酯
  参考文献：
  名称：

  The Heck–Matsuda arylation of 2-hetero-substituted acrylates

  摘要：

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.132
• 作为产物：
  描述：

  甲醇 、 2-乙酰胺基丙烯酸甲酯 、 4-fluorobenzenediazonium tetrafluoroborate 在 2,6-二叔丁基-4-甲基吡啶 、 palladium diacetate 作用下， 以68%的产率得到2-乙酰氨基-3-(4-氟苯基)-2-甲氧基丙酸甲酯
  参考文献：
  名称：

  The Heck–Matsuda arylation of 2-hetero-substituted acrylates

  摘要：

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.132