4-(7-羟基-4-氧代-4H-苯并吡喃-3-基)苯基己酸酯 | 602329-51-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 4-(7-羟基-4-氧代-4H-苯并吡喃-3-基)苯基己酸酯
• 英文名称: 4'-O-hexanoyl-daidzein
• 英文别名: 4'-O-hexanoyldaidzein；Hexanoic Acid 4-(7-Hydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl Ester；[4-(7-hydroxy-4-oxochromen-3-yl)phenyl] hexanoate
• CAS: 602329-51-1
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: QHOPMOMDTCSQMX-UHFFFAOYSA-N

物化性质

• 熔点：
  154-157°C
• 溶解度：
  可溶于二氯甲烷、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(7-羟基-4-氧代-4H-苯并吡喃-3-基)苯基己酸酯 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 豆苷
  参考文献：
  名称：

  Facile Synthesis of Flavonoid 7-O-Glycosides

  摘要：

  Highly regioselective removal of the 7-O-acylgroups of the peracyated flavones, isoflavones, and flavonolsyl(PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF3.Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.

  DOI：

  10.1021/jo034553e
• 作为产物：
  描述：

  大豆甙元 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 苯硫酚 作用下， 以 N-甲基吡咯烷酮 、 氯仿 为溶剂， 生成 4-(7-羟基-4-氧代-4H-苯并吡喃-3-基)苯基己酸酯
  参考文献：
  名称：

  Facile Synthesis of Flavonoid 7-O-Glycosides

  摘要：

  Highly regioselective removal of the 7-O-acylgroups of the peracyated flavones, isoflavones, and flavonolsyl(PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF3.Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.

  DOI：

  10.1021/jo034553e

文献信息

• An Efficient Method for the Glycosylation of Isoflavones
  作者：Nawaf Al-Maharik、Nigel P. Botting

  DOI：10.1002/ejoc.200800803

  日期：2008.11

  A new efficient, high-yielding glycosylation procedure is described for isoflavones, which employs 2,2,2-trifluoro-N-(p-methoxyphenyl)acetamidates as the glycosyl donors. This methodology was used to prepare the 7-O-glycosides of the three main isoflavones, daidzein, genistein and glycitein. The isoflavones were protected with hexanoyl groups which improved their solubility in organic solvents and

  异黄酮植物雌激素因其正面和负面的健康益处而受到当前的关注。然而，关于它们的吸收、代谢和生物利用度，仍有许多悬而未决的问题。该领域的研究需要获取异黄酮 7-O-葡萄糖苷（在植物中发现的形式）和 7-O-葡萄糖醛酸苷（它们是重要的哺乳动物代谢物）的样本。描述了一种新的高效、高产的异黄酮糖基化程序，它采用 2,2,2-三氟-N-（对甲氧基苯基）乙酰胺作为糖基供体。该方法用于制备三种主要异黄酮、黄豆苷元、染料木黄酮和黄豆黄素的 7-O-糖苷。异黄酮用己酰基保护，这提高了它们在有机溶剂中的溶解度并提高了反应效率。然后采用相同的方法合成类似的 7-O-葡糖苷酸。新的合成将为进一步的生物学研究提供大量这些化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• A facile synthesis of isoflavone 7-O-glucuronides
  作者：Nawaf Al-Maharik、Nigel P. Botting

  DOI：10.1016/j.tetlet.2006.10.034

  日期：2006.12

  An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• Highly regioselective dehexanoylation in fully hexanoylated flavonoids
  作者：Zhiwei Zheng、Ziyi Han、Li Cai、Dandan Zhou、Bryson R. Chavis、Changsheng Li、Qiang Sui、Kaiyuan Jiang、Qi Gao

  DOI：10.1016/j.tetlet.2018.11.015

  日期：2018.12

  Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH-CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation. (C) 2018 Elsevier Ltd. All rights reserved.
• Facile Synthesis of Flavonoid 7-<i>O</i>-Glycosides
  作者：Ming Li、Xiuwen Han、Biao Yu

  DOI：10.1021/jo034553e

  日期：2003.8.1

  Highly regioselective removal of the 7-O-acylgroups of the peracyated flavones, isoflavones, and flavonolsyl(PhSH, imidazole, NMP) followed by effective glycosylation with glycosyl trifluoroacetimidates (BF3.Et2O) and cautious deprotection of the acyl groups under basic conditions afforded the desired 7-O-flavonoid glycosides in satisfactory yields.