4-(3,7-bis(benzoyloxy)-5-hydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-(3,7-bis(benzoyloxy)-5-hydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate
• 英文别名: [2-Benzoyloxy-4-[3,7-dibenzoyloxy-5-hydroxy-6-(3-methylbut-2-enyl)-4-oxochromen-2-yl]phenyl] benzoate；[2-benzoyloxy-4-[3,7-dibenzoyloxy-5-hydroxy-6-(3-methylbut-2-enyl)-4-oxochromen-2-yl]phenyl] benzoate
• 化学式: C₄₈H₃₄O₁₁
• 分子量: 786.791
• InChiKey: FLUBFQSYWWCMLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  59
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(3,7-bis(benzoyloxy)-5-hydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate 在 sodium methylate 、 三乙胺 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以74%的产率得到2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl benzoate
  参考文献：
  名称：

  Synthesis of poinsettifolin A

  摘要：

  A synthesis of poinsettifolin A (1), a prenylated flavonol isolated from Dorstenia poinsettifolia, is described. Two routes starting from quercetin were explored, and 1 could be prepared if a prenyl group first was incorporated at C-6 of the protected quercetin followed by a condensation with citral at C-8. The key synthetic steps are a Mitsunobu reaction, an europium (III)-catalysed Claisen rearrangement coupled with cross-metathesis, and a benzopyran-forming geranylation. The two geranylated 3,5,3',4'-tetrahydroxyflavonols prepared, 1 and 3, were assayed for antileishmanial activity against Leishmania amazonensis and Leishmania braziliensis, and found to be active. Compound 3 showed cytotoxic activity against leukaemia and lung cancer cells while 1 lacked cytotoxicity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.021
• 作为产物：
  描述：

  4-(3,7-bis(benzoyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 63.0h， 生成 4-(3,7-bis(benzoyloxy)-5-hydroxy-6-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate
  参考文献：
  名称：

  Synthesis of poinsettifolin A

  摘要：

  A synthesis of poinsettifolin A (1), a prenylated flavonol isolated from Dorstenia poinsettifolia, is described. Two routes starting from quercetin were explored, and 1 could be prepared if a prenyl group first was incorporated at C-6 of the protected quercetin followed by a condensation with citral at C-8. The key synthetic steps are a Mitsunobu reaction, an europium (III)-catalysed Claisen rearrangement coupled with cross-metathesis, and a benzopyran-forming geranylation. The two geranylated 3,5,3',4'-tetrahydroxyflavonols prepared, 1 and 3, were assayed for antileishmanial activity against Leishmania amazonensis and Leishmania braziliensis, and found to be active. Compound 3 showed cytotoxic activity against leukaemia and lung cancer cells while 1 lacked cytotoxicity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.021