4',5,7-triacetoxy-6-(3-methyl-2-butenyl)isoflavone | 51225-29-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4',5,7-triacetoxy-6-(3-methyl-2-butenyl)isoflavone
• 英文别名: 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone；Erythinin-B-triacetat；[4-[5,7-Diacetyloxy-6-(3-methylbut-2-enyl)-4-oxochromen-3-yl]phenyl] acetate
• CAS: 51225-29-7
• 化学式: C₂₆H₂₄O₈
• 分子量: 464.472
• InChiKey: XJQGAEOCMQGCOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4,2',4'-tris(benzyloxy)-6'-benzyloxy-3'-iodochalcone 在 palladium on activated charcoal 、 palladium dichloride 吡啶 、 甲醇 、 sodium hydroxide 、 copper(l) iodide 、 羟基甲苯磺酰碘苯 、 氢气 、 三氯化硼 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 39.75h， 生成 4',5,7-triacetoxy-6-(3-methyl-2-butenyl)isoflavone
  参考文献：
  名称：

  Regioselective Synthesis of 6‐Prenylpolyhydroxyisoflavone (Wighteone) and Wighteone Hydrate with Hypervalent Iodine

  摘要：

  The oxidative rearrangement of 3'-iodotetraalkoxychalcone with [hydroxyl(tosyloxy)iodo]benzene, followed by cyclization of the resultant acetal gave 6-iodotrialkoxyisoflavone. The coupling reaction of the isoflavone with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone, whose hydrogenation gave wighteone hydrate. Wighteone was synthesized by dehydration of wighteone hydrate.

  DOI：

  10.1080/00397910500514121

文献信息

• Indonesian Medicinal Plants. XXI. Inhibitors of Na+/H+ Exchanger from the Bark of Erythrina variegata and the Roots of Maclura cochinchinensis.
  作者：Motomasa KOBAYASHI、Taifo MAHMUD、Naoki YOSHIOKA、Hirotaka SHIBUYA、Isao KITAGAWA

  DOI：10.1248/cpb.45.1615

  日期：——

  Through bioassay-guided separation of the methanol extracts of Indonesian medicinal plants, three inhibitors of the Na+/H+ exchange system, erythrinin B (2), euchrenone b10 (3), and 1, 3, 5-trihydroxy-4-(3-methylbut-2-enyl)xanthen-9-one (4), were isolated from the bark of Erythrina variegata (Fabaceae)(for 2) and the roots of Maclura cochinchinensis (Moraceae)(for 2, 3, 4). Compounds 2, 3, and 4 significantly inhibited the Na+/H+ exchanges system of arterial smooth muscle cells, with minimum inhibitory concentrations of 1.25, 1.25, and 10μg/ml, respectively. Three new prenylated xanthones named isocudraniaxanthones B (5) and A (7) and isoalvaxanthone (9) were also isolated from M. cochinchinensis and the chemical structures were elucidated on the bases of their chemical and physicochemical properties.

  通过生物测定法分离印度尼西亚药用植物的甲醇提取物，从刺桐（Fabaceae）树皮（化合物2）和木荷（Moraceae）根（化合物2、3、4）中分离出三种钠/氢离子交换系统抑制剂：刺桐素B（2）、刺桐素B10（3）和1,3,5-三羟基-4-(3-甲基丁-2-烯基)氧杂蒽-9-酮（4）。化合物2、3和4显著抑制动脉平滑肌细胞的钠/氢离子交换系统，最小抑制浓度分别为1.25、1.25和10μg/ml。从木荷中分离出三种新的异戊烯基氧杂蒽酮，分别是异刺桐素氧杂蒽酮B（5）、异刺桐素氧杂蒽酮A（7）和异刺桐素氧杂蒽酮（9），并根据其化学和物理化学性质阐明了其化学结构。
• Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents
  作者：Mohammad M. Hossain、Yasuhiko Kawamura、Kazuyo Yamashita、Masao Tsukayama

  DOI：10.1016/j.tet.2006.06.066

  日期：2006.9

  Microwave-assisted oxidative rearrangement of 3'-iodotetraalkoxychalcones with hypervalent iodine such as [hydroxy(tosyloxy)iodo]benzene or [bis(trifluoroacetoxy)iodo] benzene, followed by microwave-mediated hydrolysis and in situ cyclization of the resultant acetals gave 6-iodotrialkoxyisoflavones. Pd(0)-catalyzed coupling reaction of the 6-iodoisoflavones with 2-methyl-3-butyn-2-of under microwave irradiation gave 6-alkynylisoflavones, whose hydrogenation gave the respective hydrates of wighteone, lupisoflavone and derrubone. Wighteone (1a), lupisoflavone (1b) and derrubone (1c) were obtained by dehydration of their respective hydrates under microwave irradiation. (c) 2006 Elsevier Ltd. All rights reserved.
• Regioselective Synthesis of 6‐Prenylpolyhydroxyisoflavone (Wighteone) and Wighteone Hydrate with Hypervalent Iodine
  作者：Takanori Tokuoka、Kazuyo Yamashita、Yasuhiko Kawamura、Masao Tsukayama、Mohammad M. Hossain

  DOI：10.1080/00397910500514121

  日期：2006.5

  The oxidative rearrangement of 3'-iodotetraalkoxychalcone with [hydroxyl(tosyloxy)iodo]benzene, followed by cyclization of the resultant acetal gave 6-iodotrialkoxyisoflavone. The coupling reaction of the isoflavone with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone, whose hydrogenation gave wighteone hydrate. Wighteone was synthesized by dehydration of wighteone hydrate.