Benzyl 3,4-dihydroxy-5-phenylmethoxybenzoate | 169229-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzyl 3,4-dihydroxy-5-phenylmethoxybenzoate
• 英文别名: benzyl 3,4-dihydroxy-5-phenylmethoxybenzoate
• CAS: 169229-60-1
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: WCAOMXLYRDKAAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl 3,4-dihydroxy-5-phenylmethoxybenzoate 在 邻四氯苯醌 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 20.0h， 生成 benzyl 5-(benzyloxy)-2-(S-cysteinyl)-3,4-dihydroxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u
• 作为产物：
  描述：

  三乙酰基没食子酰氯 在 4-二甲氨基吡啶 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 31.5h， 生成 Benzyl 3,4-dihydroxy-5-phenylmethoxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u