chrysin dibenzoate | 110865-06-0

• 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: chrysin dibenzoate
• 英文别名: 5,7-di-O-benzoyl chrysin；5,7-dibenzoyloxyflavone；5,7-bis-benzoyloxy-2-phenyl-chromen-4-one；5,7-Bis-benzoyloxy-2-phenyl-chromen-4-on；4H-1-Benzopyran-4-one, 5,7-bis(benzoyloxy)-2-phenyl-；(5-benzoyloxy-4-oxo-2-phenylchromen-7-yl) benzoate
• CAS: 110865-06-0
• 化学式: C₂₉H₁₈O₆
• 分子量: 462.458
• InChiKey: XGEYPCLLAKGAQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  680.4±55.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  chrysin dibenzoate 在 sodium methylate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以65%的产率得到白杨素
  参考文献：
  名称：

  合成二羟基黄酮（菊酯，乙酰乙酸等）

  摘要：

  DOI：

  10.1016/s0040-4039(00)85249-1
• 作为产物：
  描述：

  白杨素 、 苯甲酰氯 在 吡啶 作用下， 以65%的产率得到chrysin dibenzoate
  参考文献：
  名称：

  Synthesis and antitumor activity evaluation of chrysin derivatives

  摘要：

  A series of 5,7-disubstituted chrysin, 7-monosubstituted chrysin, 5-monosubstituted chrysin derivatives were synthesized by alkylation, acetylation, benzoylation, carboxymethylation, and evaluated on their antitumor activity of H22 cells in the search for potential antitumor agents. Among them, compound 3 (5,7-diacetyl chrysin) displayed the most potent antitumor activity with IC50 value of 141 mu M. Moreover, there is significant up-regulation of G2 in cell cycle of H22. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.044

文献信息

• Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
  作者：Benjamin J. Compton、Lesley Larsen、Rex T. Weavers

  DOI：10.1016/j.tet.2010.11.076

  日期：2011.1

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 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.
• FLOCH V. LE; LEFEUVRE M., TETRAHEDRON LETT., 27,(1986) N 45, 5503-5504
  作者：FLOCH V. LE、 LEFEUVRE M.

  DOI：——

  日期：——