Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3,5-Dihydroxy-7,8-dimethoxyflavones from 3-Hydroxy-5,7,8-trimethoxyflavones(Organic,Chemical)
スポンサーリンク
概要
- 論文の詳細を見る
2-Hydroxy-3,4,6-trimethoxy-ω-(p-methoxybenzoyloxy)acetophenone was prepared from 2,3,4,6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with p-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4',5,7,8-tetramethoxyflavone along with 2-(a-hydroxy-4-methoxybenzylidene)-4,6,7-trimethoxycoumaranone. The 5-methoxy group in the tosylate or mesylate of the 3-hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give the corresponding 5-hydroxyflavone, which was converted into 3,5-dihydroxy-4',7,8-trimethoxyflavone with anhydrous potassium carbonate in methanol. 3,3',4',5-Tetrahydroxy-7,8-dimethoxyflavone was also synthesized by a similar method. The demethylation of the 5-methoxy group in flavones with a 3-hydroxy group is applicable to the synthesis of 3,5-dihydroxyflavones.
- 社団法人日本薬学会の論文
- 1987-11-25
著者
-
山本 茂生
Department Of Applied Chemistry Faculty Of Engineering Tokushima University
-
津嘉山 正夫
徳島大学工学部
-
河村 保彦
徳島大学大学院ソシオテクノサイエンス研究部
-
堀江 徳愛
Department of Applied Chemistry, Faculty of Engineering, Tokushima University
-
津嘉山 正夫
Department of Applied Chemistry, Faculty of Engineering, Tokushima University
-
河村 保彦
Department of Applied Chemistry, Faculty of Engineering, Tokushima University
-
津嘉山 正夫
Department Of Chemical Science And Technology Faculty Of Engineering The University Of Tokushima
-
堀江 徳愛
Department Of Applied Chemistry Faculty Of Engineering Tokushima University
-
堀江 徳愛
Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
関連論文
- マイクロ波照射による柑橘ユコウ乾燥果皮からのポリメトキシフラボンの迅速・効率的抽出
- マイクロ波有機合成の基礎と応用
- 5,7-ジヒドロキシ-4', 8-ジメトキシフラボンの合成 : CirsitakaogeninとCirsitakaosideの構造の訂正
- マイクロ波照射によるスダチ搾汁残渣中のフラボン成分の迅速抽出および有用物質への変換
- 91 スダチ中の新フラボン配糖体の構造
- Antiviral Activity of Natural Occurring Flavonoids in Vitro
- Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3,5-Dihydroxy-7,8-dimethoxyflavones from 3-Hydroxy-5,7,8-trimethoxyflavones(Organic,Chemical)
- Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XII. : A New, Convenient Method for Synthesizing 3,5-Dihydroxy-6,7-dimethoxyflavones from 3,5,6,7-Tetramethoxyflavones
- 2, 6-ジ置換 2H-ピラン-3(6H)-オン類のマンニッヒ塩基の合成と殺ダニ活性
- Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. VIII. : Synthesis of Pedaliin
- フラボノイドの選択的O-アルキル化及び脱アルキル化反応に関する研究(第7報)5,6,7-三置換フラボン類の部分脱アルキル化反応及びPectolinarigeninとその同族体の合成
- Synthesis of Pyranoisoflavones by the Oxidative Rearrangement of Dihydropyranochalcones with Thallium(III) Nitrate : Synthesis of Elongatin, its Angular Isomer, Toxicarol Isoflavone, and Related Compounds
- A Convenient Synthesis of Prenylated Isoflavones : Synthesis of Licoricone and Related Compounds
- Inhibition of Intestinal α-Glucosidases and Sugar Absorption by Flavones
- Inhibition of Aldose Reductase by 3', 4'-Dihydroxyflavones
- 3′,4′,5-トリヒドロキシ-6,7,8-トリメトキシフラボンおよび関連化合物の合成(ノ-ト)
- Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XIX. A Convenient Method for Synthesizing 3,5,6,7,8-Pentaoxygenated Flavones
- Synthesis of Parvisoflavones A and B
- 生体透過性近赤外光で活性化される抗シュヨウ性分子の合成と機能
- 阿波藍に含有される有用微量成分の有効利用に関する研究