diethyl (acetylamino)<2-(2-nitro-3-hydroxyphenyl)-2-oxoethyl>propanedioate | 224044-63-7

• 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: diethyl (acetylamino)<2-(2-nitro-3-hydroxyphenyl)-2-oxoethyl>propanedioate
• 英文别名: Diethyl 2-acetamido-2-[2-(3-hydroxy-2-nitrophenyl)-2-oxoethyl]propanedioate
• CAS: 224044-63-7
• 化学式: C₁₇H₂₀N₂O₉
• 分子量: 396.354
• InChiKey: WSNKSZZIDXOVOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  165
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl (acetylamino)<2-(2-nitro-3-hydroxyphenyl)-2-oxoethyl>propanedioate 在 palladium on activated charcoal 氢气 、 sodium ethanolate 、 氰化汞 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 2-Acetylamino-2-{2-[2-amino-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-2-oxo-ethyl}-malonic acid
  参考文献：
  名称：

  Synthesis of Human Ultraviolet Filter Compounds:  O-β-d-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid

  摘要：

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.

  DOI：

  10.1021/jo982321n
• 作为产物：
  描述：

  2-nitro-3-benzyloxyacetophenone 在 sodium ethanolate 、 溴-1,4-二氧六环复合物 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 diethyl (acetylamino)<2-(2-nitro-3-hydroxyphenyl)-2-oxoethyl>propanedioate
  参考文献：
  名称：

  Synthesis of Human Ultraviolet Filter Compounds:  O-β-d-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid

  摘要：

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.

  DOI：

  10.1021/jo982321n

文献信息

• Synthesis of Human Ultraviolet Filter Compounds:  <i>O</i>-β-<scp>d</scp>-Glucopyranosides of 3-Hydroxykynurenine and 2-Amino-3-hydroxy-γ-oxobenzenebutanoic Acid
  作者：Michael K. Manthey、Joanne F. Jamie、Roger J. W. Truscott

  DOI：10.1021/jo982321n

  日期：1999.5.1

  The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-beta-D-glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-gamma-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3-hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the alpha-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3-benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.