(2E)-4-(3-羟基-2-硝基苯基)-4-氧代-2-丁烯酸甲酯 | 224044-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (2E)-4-(3-羟基-2-硝基苯基)-4-氧代-2-丁烯酸甲酯
• 英文名称: methyl (E)-4-oxo-4-(3-hydroxy-2-nitrophenyl)-2-butenoate
• 英文别名: (2E)-4-(3-Hydroxy-2-nitrophenyl)-4-oxo-2-butenoic Acid Methyl Ester；methyl (E)-4-(3-hydroxy-2-nitrophenyl)-4-oxobut-2-enoate
• CAS: 224044-67-1
• 化学式: C₁₁H₉NO₆
• 分子量: 251.196
• InChiKey: HNATUFITVBWQHT-AATRIKPKSA-N

物化性质

• 溶解度：
  可溶于乙腈、氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-4-(3-羟基-2-硝基苯基)-4-氧代-2-丁烯酸甲酯 在 platinum(IV) oxide 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 18.0h， 生成 4-[2-Amino-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-butyric acid methyl ester
  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：

  甲醇 、 4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(2E)-4-(3-羟基-2-硝基苯基)-4-氧代-2-丁烯酸甲酯
  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.