7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone | 887149-31-7

• 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: 7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone
• 英文别名: 4',7-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone；[4-[7-Benzoyloxy-5-hydroxy-6-(3-methylbut-2-enyl)-4-oxochromen-3-yl]phenyl] benzoate
• CAS: 887149-31-7
• 化学式: C₃₄H₂₆O₇
• 分子量: 546.576
• InChiKey: BFHLYXKJBPIKKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.33h， 以72%的产率得到Wighteone; 5,7,4'三羟基-6-异戊烯基异黄酮
  参考文献：
  名称：

  Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.06.066
• 作为产物：
  描述：

  4,2',4'-tris(benzyloxy)-6'-benzyloxy-3'-iodochalcone 在 palladium on activated charcoal 、 palladium dichloride 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 37.42h， 生成 7,4'-bis(benzoyloxy)-5-hydroxy-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