lanceolone | 104703-99-3

• 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: lanceolone
• 英文别名: derrone; 5-Me ether；3-(4-Hydroxy-phenyl)-5-methoxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-4-one；3-(4-Hydroxyphenyl)-5-methoxy-8,8-dimethylpyrano[2,3-h]chromen-4-one
• CAS: 104703-99-3
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: YHHXGURSYSXKNO-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：

  乙酸酐 、 lanceolone 以 吡啶 为溶剂， 以7 mg的产率得到Acetic acid 4-(5-methoxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-3-yl)-phenyl ester
  参考文献：
  名称：

  披针草的新的苯甲酰葡萄糖苷和新的异戊烯基异黄酮

  摘要：

  从Lophira lanceolata的风干叶中分离出一种新的苯甲酰基葡糖苷，lanceoloside A（1），和一种新的异戊烯酮化异黄酮，lanceolone（2）。两种结构都是根据光谱和化学证据确定的。

  DOI：

  10.1021/np970370+
• 作为产物：
  描述：

  3-(4-Benzyloxy-phenyl)-5-methoxy-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 1.0h， 生成 lanceolone
  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

• Synthesis of 4',5- and 3',4',5-Oxygenated Pyranoisoflavones: Alpinumisoflavone and Related Compounds, and a Revised Structure of Derrone
  作者：Masao Tsukayama、Yasuhiko Kawamura、Hideo Tahara

  DOI：10.3987/com-91-5918

  日期：——

  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.
• A New Benzoylglucoside and a New Prenylated Isoflavone from <i>Lophira lanceolata</i>
  作者：D. E. Pegnyemb、B. B. Messanga、R. Ghogomu、B. L. Sondengam、M. T. Martin、B. Bodo

  DOI：10.1021/np970370+

  日期：1998.6.1

  A new benzoylglucoside, lanceoloside A (1), and a new prenylated isoflavone, lanceolone (2), have been isolated from the air-dried leaves of Lophira lanceolata. Both structures were established from spectroscopic and chemical evidence.

  从Lophira lanceolata的风干叶中分离出一种新的苯甲酰基葡糖苷，lanceoloside A（1），和一种新的异戊烯酮化异黄酮，lanceolone（2）。两种结构都是根据光谱和化学证据确定的。