1-(Benzyloxy)-3-<(methoxycarbonyl)ethyl>-5,6-dimethyl-2(1H)-pyrazinone | 162610-60-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(Benzyloxy)-3-<(methoxycarbonyl)ethyl>-5,6-dimethyl-2(1H)-pyrazinone
• 英文别名: Methyl 3-(5,6-dimethyl-3-oxo-4-phenylmethoxypyrazin-2-yl)propanoate
• CAS: 162610-60-8
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: GLXCGYQGYWXZRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Benzyloxy)-3-<(methoxycarbonyl)ethyl>-5,6-dimethyl-2(1H)-pyrazinone 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-<3-<1-(Benzyloxy)-5,6-dimethyl-2-oxo-1,2-dihydropyraz-3-yl>propanoyl>-L-alanine methyl ester
  参考文献：
  名称：

  N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine

  摘要：

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.

  DOI：

  10.1021/jo00111a015
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-甲酯 在 盐酸 、 sodium hydroxide 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.25h， 生成 1-(Benzyloxy)-3-<(methoxycarbonyl)ethyl>-5,6-dimethyl-2(1H)-pyrazinone
  参考文献：
  名称：

  N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine

  摘要：

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.

  DOI：

  10.1021/jo00111a015

文献信息

• N-Hydroxyamide-Containing Heterocycles. Part 4. Synthesis and FeIII-Chelating Properties of Novel Hexadentate Ligands Composed of N-Hydroxy-2(1H)-Pyrazinone, Amino Acid Residues, and Tris(2-aminoethyl)amine
  作者：Junko Ohkanda、Akira Katoh

  DOI：10.1021/jo00111a015

  日期：1995.3

  Synthesis of novel hexadentate ligands (3-HOPR(X); X = Me and Bu(i)) composed of N-hydroxy-2(1H)-pyrazinone, amino acids, and tris(2-aminoethyl)amine, and their Fe-III-chelating properties are described. N-(Benzyloxy)-2(VF)-pyrazinone (6) bearing the carboxyl group at C-3 position of the pyrazinone ring was synthesized from L-glutamic acid vip five steps. The consecutive coupling of 6 with amino acids and tris(2-aminoethyl)amine, followed by the deprotection of the O-benzyl group, afforded target compounds (3-HOPR(X)). UV-vis spectral data of the 1:1 molar mixture of 3-HOPR(X) and Fe-III in aqueous solution indicated the formation of intramolecular 1:3 Fe-III complex to the hydroxamate units. The relative stability constants (log K 21-22) of the complexes were influenced by the side chains of L-amino acid residues. Further, the absolute configuration around Fe-III was dramatically changed, viz., Fe(3-opr(Me)) exists predominantly in the Lambda-cis configuration, while Fe(3-opr(Bu(i))) exist in the Delta-cis in water. From the Fe-III removal experiment of 3-HOPR(X) from transferrin at pH 7.4, it was concluded that 3-HOPR(X) was a more effective Fe-III removal agent than the naturally occurring siderophore, desferrioxamine B.