4,5-dimethoxy-2-(3'-iodo-4'-methoxybenzoyloxy)acetophenone | 95275-62-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4,5-dimethoxy-2-(3'-iodo-4'-methoxybenzoyloxy)acetophenone
• 英文别名: 3-Jod-p-anissaeure-<3.5-dimethoxy-2-acetyl-phenylester>；3-Jod-p-anissaeure-(3.5-dimethoxy-2-acetyl-phenylester)；2-Acetyl-3,5-dimethoxyphenyl 3-iodo-4-methoxybenzoate；(2-acetyl-3,5-dimethoxyphenyl) 3-iodo-4-methoxybenzoate
• CAS: 95275-62-0
• 化学式: C₁₈H₁₇IO₆
• 分子量: 456.234
• InChiKey: YCAHNBZQJQRSFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-(3'-iodo-4'-methoxybenzoyloxy)acetophenone 在 氢氧化钾 、 硫酸 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 0.34h， 生成 3'-Jod-4',5,7-trimethoxy-flavon
  参考文献：
  名称：

  Total Synthesis of Robustaflavone, a Potential Anti-Hepatitis B Agent

  摘要：

  Robustaflavone, a naturally occurring compound, is an inhibitor of hepatitis B virus replication in vitro. Robustaflavone is a biflavanoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a biaryl linkage between the g-position of one unit and the 3'-position of the other (I6,II3'-biapigenin). The natural material was isolated from the seed-kernels of Rhus succedanea. To provide ready access to sufficient quantities of material for continued biological studies, as well as to provide a general route for the preparation of structural analogues, a total synthesis of robustaflavone was pursued. The total synthesis was approached by constructing apigenin ethers containing functionalities at the 6- and 3'-positions which could be cross-coupled using transition metal catalysis. Key steps of the synthesis included development of a regioselective iodination of an apigenin derivative at the 6-position. Also key was the formation of an apigenin 3'-boronate using a palladium-catalyzed exchange of the corresponding 3'-iodide with a diboron reagent. Finally, identification of appropriate reaction conditions for Suzuki coupling to form the sterically congested 6-3''' biaryl bond of robustaflavone provided access to the desired biflavanoid system. This work represents the first total synthesis of robustaflavone.

  DOI：

  10.1021/jo981186b
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4,5-dimethoxy-2-(3'-iodo-4'-methoxybenzoyloxy)acetophenone
  参考文献：
  名称：

  Nakazawa,K., Chemical and pharmaceutical bulletin, 1962, vol. 10, p. 1032 - 1038

  摘要：

  DOI：

文献信息

• Nakazawa,K., Chemical and pharmaceutical bulletin, 1962, vol. 10, p. 1032 - 1038
  作者：Nakazawa,K.

  DOI：——

  日期：——
• Total Synthesis of Robustaflavone, a Potential Anti-Hepatitis B Agent
  作者：David E. Zembower、Heping Zhang

  DOI：10.1021/jo981186b

  日期：1998.12.1

  Robustaflavone, a naturally occurring compound, is an inhibitor of hepatitis B virus replication in vitro. Robustaflavone is a biflavanoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a biaryl linkage between the g-position of one unit and the 3'-position of the other (I6,II3'-biapigenin). The natural material was isolated from the seed-kernels of Rhus succedanea. To provide ready access to sufficient quantities of material for continued biological studies, as well as to provide a general route for the preparation of structural analogues, a total synthesis of robustaflavone was pursued. The total synthesis was approached by constructing apigenin ethers containing functionalities at the 6- and 3'-positions which could be cross-coupled using transition metal catalysis. Key steps of the synthesis included development of a regioselective iodination of an apigenin derivative at the 6-position. Also key was the formation of an apigenin 3'-boronate using a palladium-catalyzed exchange of the corresponding 3'-iodide with a diboron reagent. Finally, identification of appropriate reaction conditions for Suzuki coupling to form the sterically congested 6-3''' biaryl bond of robustaflavone provided access to the desired biflavanoid system. This work represents the first total synthesis of robustaflavone.