(2E)-4-[2-硝基-3-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯基]-4-氧代-2-丁烯酸甲酯 | 224044-68-2

• 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
• 中文名称: (2E)-4-[2-硝基-3-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯基]-4-氧代-2-丁烯酸甲酯
• 英文名称: methyl (E)-4-oxo-4-<2-nitro-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate
• 英文别名: (2E)-4-[2-Nitro-3-[(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)oxy]phenyl]-4-oxo-2-butenoic Acid Methyl Ester；methyl (E)-4-[2-nitro-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]-4-oxobut-2-enoate
• CAS: 224044-68-2
• 化学式: C₂₅H₂₇NO₁₅
• 分子量: 581.487
• InChiKey: GZEJVMGQFOJCDQ-WHIUSNHVSA-N

物化性质

• 溶解度：
  可溶于丙酮、氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  213
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2E)-4-[2-硝基-3-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]苯基]-4-氧代-2-丁烯酸甲酯 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 以63%的产率得到methyl 4-oxo-4-<2-amino-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxyphenyl>-2-butenoate
  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：

  4-(3-hydroxy-2-nitrophenyl)-4-oxo-2-butenoic acid 在 氰化汞 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 (2E)-4-[2-硝基-3-[(2,3,4,6-四-O-乙酰基-beta-D-吡喃葡萄糖基)氧基]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.