7,4'-di-O-hexanoyl-daidzein | 602329-45-3

• 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: 7,4'-di-O-hexanoyl-daidzein
• 英文别名: daidzein dihexanoate；[4-(7-Hexanoyloxy-4-oxochromen-3-yl)phenyl] hexanoate
• CAS: 602329-45-3
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: LJKDSWUPSQWKAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  108.6 °C
• 沸点：
  581.9±50.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,4'-di-O-hexanoyl-daidzein 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以88%的产率得到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：

  Highly regioselective dehexanoylation in fully hexanoylated flavonoids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2018.11.015
• 作为产物：
  描述：

  大豆甙元 、 己酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 以77%的产率得到7,4'-di-O-hexanoyl-daidzein
  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

• 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.
• 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.