diethyl (acetylamino)<2-(2-nitro-3-phenylmethoxyphenyl)-2-oxoethyl>propanedioate | 224044-62-6

• 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-phenylmethoxyphenyl)-2-oxoethyl>propanedioate
• 英文别名: 2-(Acetylamino)-2-[2-[2-nitro-3-(phenylmethoxy)phenyl]-2-oxoethyl]propanedioic Acid 1,3-Diethyl Ester；diethyl 2-acetamido-2-[2-(2-nitro-3-phenylmethoxyphenyl)-2-oxoethyl]propanedioate
• CAS: 224044-62-6
• 化学式: C₂₄H₂₆N₂O₉
• 分子量: 486.478
• InChiKey: CGLSCGDZMYKKLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl (acetylamino)<2-(2-nitro-3-phenylmethoxyphenyl)-2-oxoethyl>propanedioate 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium ethanolate 、 氰化汞 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 α-acetylamino-2-amino-3-(β-D-glucopyranosyloxy)oxobenzenebutanoic 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 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 diethyl (acetylamino)<2-(2-nitro-3-phenylmethoxyphenyl)-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.