5-Benzyloxy-2,3-dioxo-pentanoic acid (4-methoxy-benzyl)-[(4-methoxy-benzylcarbamoyl)-methyl]-amide | 144581-90-8

• 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: 5-Benzyloxy-2,3-dioxo-pentanoic acid (4-methoxy-benzyl)-[(4-methoxy-benzylcarbamoyl)-methyl]-amide
• 英文别名: N-[(4-methoxyphenyl)methyl]-N-[2-[(4-methoxyphenyl)methylamino]-2-oxoethyl]-2,3-dioxo-5-phenylmethoxypentanamide
• CAS: 144581-90-8
• 化学式: C₃₀H₃₂N₂O₇
• 分子量: 532.593
• InChiKey: UIKGKLWTRISESO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Benzyloxy-2,3-dioxo-pentanoic acid (4-methoxy-benzyl)-[(4-methoxy-benzylcarbamoyl)-methyl]-amide 以 苯 为溶剂， 以96%的产率得到3-(3-Benzyloxy-propionyl)-3-hydroxy-1,4-bis-(4-methoxy-benzyl)-piperazine-2,5-dione
  参考文献：
  名称：

  Oxidation of α-ylido, β-keto amides to vicinal tricarbonyls. Synthesis of a diketopiperazine precursor of bicyclomycin.

  摘要：

  The Yoshimura intermediate in the total synthesis of bicyclomycin was prepared by intramolecular addition of an amide to an alpha,beta-diketoamide. The resulting unsymmetrical diketopiperazine was then converted to the diol ether target.

  DOI：

  10.1016/s0040-4039(00)79110-6
• 作为产物：
  描述：

  2-bromo-N-(4-methoxybenzyl)acetamide 在 sodium hydroxide 、 臭氧 、 牛血清白蛋白 、 N,N'-二环己基碳二亚胺 、 苏丹红 作用下， 以 水 为溶剂， 生成 5-Benzyloxy-2,3-dioxo-pentanoic acid (4-methoxy-benzyl)-[(4-methoxy-benzylcarbamoyl)-methyl]-amide
  参考文献：
  名称：

  Oxidation of α-ylido, β-keto amides to vicinal tricarbonyls. Synthesis of a diketopiperazine precursor of bicyclomycin.

  摘要：

  The Yoshimura intermediate in the total synthesis of bicyclomycin was prepared by intramolecular addition of an amide to an alpha,beta-diketoamide. The resulting unsymmetrical diketopiperazine was then converted to the diol ether target.

  DOI：

  10.1016/s0040-4039(00)79110-6

文献信息

• Oxidation of α-ylido, β-keto amides to vicinal tricarbonyls. Synthesis of a diketopiperazine precursor of bicyclomycin.
  作者：Harry H. Wasserman、Vincent M. Rotello、Giuseppina B. Krause

  DOI：10.1016/s0040-4039(00)79110-6

  日期：1992.9

  The Yoshimura intermediate in the total synthesis of bicyclomycin was prepared by intramolecular addition of an amide to an alpha,beta-diketoamide. The resulting unsymmetrical diketopiperazine was then converted to the diol ether target.