2-acetamido-2-anilinoacetic acid benzyl ester | 446271-48-3

• 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: 2-acetamido-2-anilinoacetic acid benzyl ester
• 英文别名: Benzyl 2-acetamido-2-anilinoacetate
• CAS: 446271-48-3
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: WDVKZDIJPZWGSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-anilinoacetic acid benzyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以79%的产率得到2-acetamido-2-anilinoacetic acid sodium salt
  参考文献：
  名称：

  Toward Synthesis of α-Alkyl Amino Glycines (A3G), New Amino Acid Surrogates

  摘要：

  A general method giving access to protected alpha-alkyl amino glycines (A3G) 4 from the previously described precursor alpha-isopropylthioglycine I is described. In the presence of N-bromosuccinimide, displacement of the thiol by a large variety of amines afforded the corresponding racemic amino acid mimics. The efficiency of the reaction was strongly dependent on the protective groups of the nucleophile used in the condensation.

  DOI：

  10.1021/jo020154s
• 作为产物：
  描述：

  benzyl N-acetyl-α-hydroxyglycinate 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 2-acetamido-2-anilinoacetic acid benzyl ester
  参考文献：
  名称：

  Toward Synthesis of α-Alkyl Amino Glycines (A3G), New Amino Acid Surrogates

  摘要：

  A general method giving access to protected alpha-alkyl amino glycines (A3G) 4 from the previously described precursor alpha-isopropylthioglycine I is described. In the presence of N-bromosuccinimide, displacement of the thiol by a large variety of amines afforded the corresponding racemic amino acid mimics. The efficiency of the reaction was strongly dependent on the protective groups of the nucleophile used in the condensation.

  DOI：

  10.1021/jo020154s

文献信息

• Toward Synthesis of α-Alkyl Amino Glycines (A3G), New Amino Acid Surrogates
  作者：Loïc Yaouancq、Loïc René、Marie-Elise Tran Huu Dau、Bernard Badet

  DOI：10.1021/jo020154s

  日期：2002.7.1

  A general method giving access to protected alpha-alkyl amino glycines (A3G) 4 from the previously described precursor alpha-isopropylthioglycine I is described. In the presence of N-bromosuccinimide, displacement of the thiol by a large variety of amines afforded the corresponding racemic amino acid mimics. The efficiency of the reaction was strongly dependent on the protective groups of the nucleophile used in the condensation.