4-(3,7-bis(benzoyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate | 1233628-03-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(3,7-bis(benzoyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene dibenzoate
• 英文别名: [2-Benzoyloxy-4-(3,7-dibenzoyloxy-5-hydroxy-4-oxochromen-2-yl)phenyl] benzoate
• CAS: 1233628-03-9
• 化学式: C₄₃H₂₆O₁₁
• 分子量: 718.673
• InChiKey: UYKHSQSAGXPPPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 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-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 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 69.0h， 生成 poinsettifolin A
  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：

  槲皮素 、 苯甲酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以60%的产率得到4-(3,7-bis(benzoyloxy)-5-hydroxy-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

文献信息

• Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
  作者：Andrea Mattarei、Lucia Biasutto、Federico Rastrelli、Spiridione Garbisa、Ester Marotta、Mario Zoratti、Cristina Paradisi

  DOI：10.3390/molecules15074722

  日期：——

  characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported

  The regioselective synthesis of several quercetin (3,3',4',5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. 通过咪唑促进的相应五酯的脱酰基作用，选择性地获得了在 7-C 上带有游离 OH 的四乙酰化槲皮素。通过结合 HSQC 和 HMBC 2D-NMR 分析，获得了两种异构四乙酰槲皮素衍生物的明确结构表征。这些分子可用作其他衍生物的区域选择性合成的起始材料。作为例子报道了天然多酚鼠李素（7-O-甲基槲皮素）和新的线粒体化合物7-（4
• Synthesis of poinsettifolin A
  作者：Zilma Escobar、Carlos Solano、Rikard Larsson、Martin Johansson、Efrain Salamanca、Alberto Gimenez、Eduardo Muñoz、Olov Sterner

  DOI：10.1016/j.tet.2014.10.021

  日期：2014.11

  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.