3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one | 141737-97-5

• 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: 3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one
• CAS: 141737-97-5
• 化学式: C₂₇H₂₂O₅
• 分子量: 426.469
• InChiKey: CZNSKZJGEJITCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 Derrone; 5-羟基-3-(4-羟基苯基)-8,8-二甲基-4H,8H-苯并[1,2-b:3,4-b']二吡喃-4-酮
  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：

  3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8,9-dihydro-pyrano[2,3-f]chromene-4,10-dione 在 sodium hydroxide 、 sodium tetrahydroborate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 3.25h， 生成 3-(4-Benzyloxy-phenyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one
  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

文献信息

• Total Syntheses and Antibacterial Studies of Natural Isoflavones: Scandenone, Osajin, and 6,8-Diprenylgenistein
  作者：Hongbo Dong、Yufei Che、Xingtong Zhu、Yi Zhong、Jiafu Lin、Jian Wang、Weihong Du、Tao Song

  DOI：10.3390/molecules29112574

  日期：——

  angular pyran isoflavones. The antibacterial activities of 1–3 were also evaluated, and all of them displayed good antibacterial activity against Gram-positive bacteria. Among them, 2 was the most potent one against MRSA, with a MIC value of 2 μg/mL, and the SEM assay indicated that the bacterial cell membranes of both MRSA and E. faecalis could be disrupted by 2. These findings suggest that this type of

  异黄酮是一类天然产物，具有多种有趣的生物特性，包括抗氧化、保肝、抗菌和抗炎活性。 Scandenone (1)、osajin (2) 和 6,8-diprenylgenistein (3) 是天然异戊二烯异黄酮，具有相同的多酚骨架。本研究以关键中间体15为原料合成天然异黄酮1-3，建立了直链和角吡喃异黄酮的立体选择性合成方法。还对1-3的抗菌活性进行了评价，它们均对革兰氏阳性菌表现出良好的抗菌活性。其中，2是对MRSA最有效的一种，其MIC值为2 μg/mL，SEM分析表明2可以破坏MRSA和粪肠球菌的细菌细胞膜。这些结果表明，异黄酮类型可以作为开发治疗革兰氏阳性细菌感染的新型抗菌剂的先导。