5-chloro-2-(2-(4-methoxyphenyl)ethynyl)phenylphosphonic acid diethyl ester | 1227161-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-chloro-2-(2-(4-methoxyphenyl)ethynyl)phenylphosphonic acid diethyl ester
• 英文别名: 4-Chloro-2-diethoxyphosphoryl-1-[2-(4-methoxyphenyl)ethynyl]benzene
• CAS: 1227161-31-0
• 化学式: C₁₉H₂₀ClO₄P
• 分子量: 378.792
• InChiKey: MEEPWFOSULZQRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(2-(4-methoxyphenyl)ethynyl)phenylphosphonic acid diethyl ester 在 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以89%的产率得到4-bromo-1-ethoxy-3-(4-methoxyphenyl)benzo[c][1,2]oxaphosphinine 1-oxide
  参考文献：
  名称：

  Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase

  摘要：

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2010.01.038
• 作为产物：
  描述：

  (4-Chloro-2-diethoxyphosphorylphenyl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 、 4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到5-chloro-2-(2-(4-methoxyphenyl)ethynyl)phenylphosphonic acid diethyl ester
  参考文献：
  名称：

  Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase

  摘要：

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2010.01.038

文献信息

• Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts
  作者：Borja Pérez-Saavedra、Nuria Vázquez-Galiñanes、Carlos Saá、Martín Fañanás-Mastral

  DOI：10.1021/acscatal.7b02434

  日期：2017.9.1

  A copper-catalyzed tandem carboarylation/cyclization of alkynyl phosphonates with diaryliodonium salts is reported. The reaction gives straightforward access to valuable cyclic enol phosphonates in good yields under mild conditions. This transformation entails an initial chemoselective arylation of the alkyne followed by an intramolecular trapping of an intermediate vinyl cation by the phosphoryl group

  据报道用二芳基碘鎓盐对炔基膦酸酯进行铜催化的串联碳芳基化/环化。该反应可在温和条件下以高收率直接获得有价值的环状烯醇膦酸酯。该转变需要炔烃的初始化学选择性芳基化，然后通过磷酸基团将中间乙烯基阳离子分子内捕获。在由1,2-二芳基炔烃生成的中间体中，通过双键进行的β-芳基重排的观察结果支持了乙烯基阳离子的中间体。
• Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase
  作者：Baojian Li、Binhua Zhou、Hailiang Lu、Lin Ma、Ai-Yun Peng

  DOI：10.1016/j.ejmech.2010.01.038

  日期：2010.5

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.