4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid dimethyl ester | 1453477-47-8

• 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-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid dimethyl ester
• 英文别名: 4-oxo-2-phenyl-4H-chromen-7-yl dimethyl phosphate
• CAS: 1453477-47-8
• 化学式: C₁₇H₁₅O₆P
• 分子量: 346.276
• InChiKey: AVIBONXPVRHDMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  459.2±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid dimethyl ester 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以74%的产率得到4-oxo-2-phenyl-4H-chromen-7-yl dihydrogen phosphate
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 碘 、 吡啶盐酸盐 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 17.0h， 生成 4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid dimethyl ester
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281

文献信息

• Palladium-catalyzed regioselective arylation of 7-hydroxyflavone with diaryliodonium salts
  作者：Yu-Ping Zhao、Jia-Lu Liao、Chen-Fu Liu

  DOI：10.1016/j.tetlet.2023.154573

  日期：2023.6

  A palladium-catalyzed regioselective arylation at the C6 position of 7-hydroxyflavone protocol was disclosed for the first time. The reaction occurs in carbamate directing group directed CH activation manner. The key to this high regioselectivity is the appropriate choice of carbamates as protecting/directing groups and H3PO4 additive in the presence of Pd (TFA)2 catalyst. Additionally, the procedure

  首次公开了钯催化的 7-羟基黄酮 C6 位区域选择性芳基化方案。该反应以氨基甲酸酯导向基团定向的CH活化方式发生。这种高区域选择性的关键是2存在下3PO4。此外，该程序为制备 6-芳基黄酮衍生物提供了一种权宜之计。
• Synthesis and biological evaluation of phosphorylated flavonoids as potent and selective inhibitors of cholesterol esterase
  作者：Yingling Wei、Ai-Yun Peng、Bo Wang、Lin Ma、Guoping Peng、Yidan Du、Jingming Tang

  DOI：10.1016/j.ejmech.2013.03.025

  日期：2014.3

  A series of phosphorylated flavonoids were synthesized and investigated in vitro as inhibitors of pancreatic cholesterol esterase (CEase) and acetylcholinesterase (AChE). The results showed that most of the synthesized compounds exhibited nanomolar potency against CEase, much better than the parent flavonoids. Furthermore, these phosphorylated flavonoids demonstrated good to high selectivity for CEase over AChE, which only showed micromolar potency inhibition of AChE. The most selective and potent inhibitor of CEase (3e) had IC50 value of 0.72 nM and 11800-fold selectivity for CEase over AChE. The structure activity relationships revealed that the free hydroxyl group at position 5 and phosphate group at position 7 of the phosphorylated flavonoids are favorable to the inhibition of CEase. The inhibition mechanism and kinetic characterization studies indicated that they are irreversible competitive inhibitors of CEase. (C) 2014 Elsevier Masson SAS. All rights reserved.