N-formyl-4-methoxyphenylglycine methyl ester | 143323-39-1

• 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: N-formyl-4-methoxyphenylglycine methyl ester
• 英文别名: Methyl 2-formamido-2-(4-methoxyphenyl)acetate
• CAS: 143323-39-1
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: UATSKJTYEZVEBA-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  421.8±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  N-formyl-4-methoxyphenylglycine methyl ester 在 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到methyl 2-isocyano-2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Mild Oxidative One-Carbon Homologation of Aldehyde to Amide

  摘要：

  One-carbon homologation of aldehyde into amide is realized in one-pot by its reaction with potassium alpha-p-methoxyphenyl-alpha-isocyano acetic acid (1c) and hydrochloride salt of dimethylamine (3a) in toluene at room temperature followed by acidic workup. In this multicomponent reaction, 1c served as donor of the CONH2 function to aldehyde, while the dimethylamine acted as a shuttle molecule to initiate/terminate the sequence and to mediate the internal redox process of one of the three-component adducts. Ready accessibility, nominal cost of the reagents, and mild conditions are attractive features of the present method.

  DOI：

  10.1021/ja0511220
• 作为产物：
  描述：

  Alpha-氨基-4-甲氧基苯乙酸 在 氯化亚砜 、 三乙胺 作用下， 反应 18.0h， 生成 N-formyl-4-methoxyphenylglycine methyl ester
  参考文献：
  名称：

  Triple Role of Phenylselenonyl Group Enabled a One-Pot Synthesis of 1,3-Oxazinan-2-ones From α-Isocyanoacetates, Phenyl Vinyl Selenones, and Water

  摘要：

  Reaction of alpha-substituted alpha-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

  DOI：

  10.1021/ja506031h