4'-hydroxy-5-methoxy-2'',2''-dimethylpyrano[5'',6'':6,7]isoflavone | 141737-82-8

• 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'-hydroxy-5-methoxy-2'',2''-dimethylpyrano[5'',6'':6,7]isoflavone
• 英文别名: 5-O-methylalpiniumisoflavone；indicanine C；7-(4-hydroxyphenyl)-5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-6-one
• CAS: 141737-82-8
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: GIVRDLOWBBXCNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-hydroxy-5-methoxy-2'',2''-dimethylpyrano[5'',6'':6,7]isoflavone 在 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 dimethylalpinumisoflavone
  参考文献：
  名称：

  Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone

  摘要：

  Alpinumisoflavone (4', 5-dihydroxy-2".2"-dimethylpyrano[5", 6"-g]isoflavone) (1a) was synthesized by regioselective reduction of 7-(4-hydroxyphenyl)-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b:5, 4-b'] dipyran-4, 6-dione (15a) with NaBH4 and dehydration of the resultant alcohol, followed by demethylation with BC13. Its angular isomer (4', 5-dihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (2a) was synthesized from 3-(4-hydroxyphenyl)-8, 9-dihydro-5-tosyloxy-8, 8-dimethyl-4H,10H-benzo [1, 2-b:3, 4-b']dipyran-4, 10-dione (27a) in a similar manner.

  DOI：

  10.3987/com-91-5918
• 作为产物：
  描述：

  (E)-7-(benzyloxy)-6-(3-(4-(benzyloxy)phenyl)acryloyl)-5-methoxy-2,2-dimethylchroman-4-one 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 对甲苯磺酸 、 sodium hydrogensulfite 、 thallium(III) nitrate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 4'-hydroxy-5-methoxy-2'',2''-dimethylpyrano[5'',6'':6,7]isoflavone
  参考文献：
  名称：

  Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone

  摘要：

  Alpinumisoflavone (4', 5-dihydroxy-2".2"-dimethylpyrano[5", 6"-g]isoflavone) (1a) was synthesized by regioselective reduction of 7-(4-hydroxyphenyl)-2, 3-dihydro-5-methoxy-2, 2-dimethyl-4H, 6H-benzo[1, 2-b:5, 4-b'] dipyran-4, 6-dione (15a) with NaBH4 and dehydration of the resultant alcohol, followed by demethylation with BC13. Its angular isomer (4', 5-dihydroxy-2", 2"-dimethylpyrano[6", 5"-h]isoflavone) (2a) was synthesized from 3-(4-hydroxyphenyl)-8, 9-dihydro-5-tosyloxy-8, 8-dimethyl-4H,10H-benzo [1, 2-b:3, 4-b']dipyran-4, 10-dione (27a) in a similar manner.

  DOI：

  10.3987/com-91-5918