robustaflavone hexamethyl ether | 28442-04-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: robustaflavone hexamethyl ether
• 英文别名: hexa-O-methyl-robustaflavone；hexa-O-methylrobustaflavone；5,7,5',7'-tetramethoxy-2'-(4-methoxy-phenyl)-2,6'-(4-methoxy-m-phenylene)-bis-chromen-4-one；Hexa-O-methyl-robustaflavon；6-[5-(5,7-Dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 28442-04-8
• 化学式: C₃₆H₃₀O₁₀
• 分子量: 622.628
• InChiKey: DRYUEKILRSDEDG-UHFFFAOYSA-N

物化性质

• 熔点：
  296-297 °C
• 沸点：
  781.4±60.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  robustaflavone hexamethyl ether 在 三溴化硼 作用下， 以 氯仿 为溶剂， 以30%的产率得到罗波斯塔双黄酮
  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：

  5-羟基-4',7-二甲氧基黄酮 在 sodium hydroxide 、 四(三苯基膦)钯 、 碘 、 thallium(I) acetate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 robustaflavone hexamethyl ether
  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

文献信息

• FATMA W.; IGBAL J.; ISMAIL H.; ISHRATULLAH K.; SHAIDA W. A.; RAHMAN W., CHEM. AND IND., 1979, NO 9, 315-316
  作者：FATMA W.、 IGBAL J.、 ISMAIL H.、 ISHRATULLAH K.、 SHAIDA W. A.、 RAHMAN W.

  DOI：——

  日期：——
• GU, YUN-LONG;XU, YA-MING;FANG, SHENG-DING;HE, QI-MIN, CHZHIU SYUEHBAO, 32,(1990) N, S. 631-636
  作者：GU, YUN-LONG、XU, YA-MING、FANG, SHENG-DING、HE, QI-MIN

  DOI：——

  日期：——