4-(3-methyl-3-phenylureido)butanoic acid

• 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: 4-(3-methyl-3-phenylureido)butanoic acid
• 英文别名: 4-[[Methyl(phenyl)carbamoyl]amino]butanoic acid
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: JCINPPLLSMIXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-methyl-3-phenylureido)butanoic acid 、 苄胺 在 N,N'-羰基二咪唑 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以78%的产率得到N-benzyl-4-(3-methyl-3-phenylureido)butanamide
  参考文献：
  名称：

  Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides

  摘要：

  The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.033
• 作为产物：
  描述：

  N-甲基-N-苯基氨基甲酰氯 、 4-氨基丁酸 在 potassium carbonate 作用下， 以 水 、 丙酮 为溶剂， 以60%的产率得到4-(3-methyl-3-phenylureido)butanoic acid
  参考文献：
  名称：

  Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides

  摘要：

  The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.033

文献信息

• Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides
  作者：Michael C. Hillier、Hai-Hua Gong、Dean S. Clyne、Martin J. Babcock

  DOI：10.1016/j.tet.2014.10.033

  日期：2014.12

  The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin. (C) 2014 Elsevier Ltd. All rights reserved.