5-((Benzyloxy)carbonyl)benzene-1,2,3-triyl Triacetate | 182183-06-8

• 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: 5-((Benzyloxy)carbonyl)benzene-1,2,3-triyl Triacetate
• 英文别名: benzyl 3,4,5-triacetyloxybenzoate
• CAS: 182183-06-8
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: SMIWDGPXGPTQMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-((Benzyloxy)carbonyl)benzene-1,2,3-triyl Triacetate 在 邻四氯苯醌 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 47.0h， 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 、 苯甲醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到5-((Benzyloxy)carbonyl)benzene-1,2,3-triyl Triacetate
  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

文献信息

• Erectile Dysfunction Treatment
  申请人：——

  公开号：US20040247698A1

  公开（公告）日：2004-12-09

  A method for extracting compositions from a natural product, their pharmaceutical compositions, the pharmaceutical compounds, and their therapeutic uses as a sexual performance enhancer, in the treatment of erectile dysfunction, and in the treatment of hypertension in humans and animals.

  一种从天然产物中提取化合物的方法，以及它们的制药组合物、制药化合物，以及它们作为性能增强剂的治疗用途，用于治疗人类和动物的勃起功能障碍和高血压。
• 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
  作者：Ken S. Feldman、Stéphane Quideau、Heidi M. Appel

  DOI：10.1021/jo961043u

  日期：1996.1.1

  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.