2-<4-(5-chloro-2-oxo-1,2-dihydropyrimidin-1-ylmethoxymethyl)benzamido>pentanedioic acid dibenzyl ester | 146307-12-2

• 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-<4-(5-chloro-2-oxo-1,2-dihydropyrimidin-1-ylmethoxymethyl)benzamido>pentanedioic acid dibenzyl ester
• 英文别名: dibenzyl (2S)-2-[[4-[(5-chloro-2-oxopyrimidin-1-yl)methoxymethyl]benzoyl]amino]pentanedioate
• CAS: 146307-12-2
• 化学式: C₃₂H₃₀ClN₃O₇
• 分子量: 604.059
• InChiKey: XJOKDXSCVOAEPQ-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  125.82
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-<4-(5-chloro-2-oxo-1,2-dihydropyrimidin-1-ylmethoxymethyl)benzamido>pentanedioic acid dibenzyl ester 在 ammonium carbonate buffer 作用下， 以 乙腈 为溶剂， 反应 9.0h， 以88%的产率得到(S)-2-[4-(5-Chloro-2-oxo-2H-pyrimidin-1-ylmethoxymethyl)-benzoylamino]-pentanedioic acid 5-benzyl ester
  参考文献：
  名称：

  Synthesis of Pyrimidine Derivatives of Amino Acids Using Pig Liver Esterase and Pancreas Lipase.

  摘要：

  The parent methyl ester of the N-1 substituted 5-chloropyrimidinone is hydrolysed by pig liver esterase to the corresponding carboxylic acid. The acid chloride as made with PCl5 in toluene, and coupling with benzyl and Methyl esters Of selected L-amino acids to the corresponding amides was done in dichloromethane in the presence of triethylamine. The benzyl and methyl ester protecting groups were hydrolysed with pancreas lipase or esterase in a pH-stat to yield the corresponding carboxylic acids.

  DOI：

  10.3891/acta.chem.scand.46-1204
• 作为产物：
  描述：

  4-(5-chloro-2-oxo-1,2-dihydropyrimidin-1-ylmethoxymethyl)benzoic acid methyl ester 在 20 nM ammoniumcarbonate buffer 、 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 44.33h， 生成 2-<4-(5-chloro-2-oxo-1,2-dihydropyrimidin-1-ylmethoxymethyl)benzamido>pentanedioic acid dibenzyl ester
  参考文献：
  名称：

  Synthesis of Pyrimidine Derivatives of Amino Acids Using Pig Liver Esterase and Pancreas Lipase.

  摘要：

  The parent methyl ester of the N-1 substituted 5-chloropyrimidinone is hydrolysed by pig liver esterase to the corresponding carboxylic acid. The acid chloride as made with PCl5 in toluene, and coupling with benzyl and Methyl esters Of selected L-amino acids to the corresponding amides was done in dichloromethane in the presence of triethylamine. The benzyl and methyl ester protecting groups were hydrolysed with pancreas lipase or esterase in a pH-stat to yield the corresponding carboxylic acids.

  DOI：

  10.3891/acta.chem.scand.46-1204