(5-methoxy-2-phenylethynyl-phenyl)-phosphonic acid diethyl ester | 639517-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5-methoxy-2-phenylethynyl-phenyl)-phosphonic acid diethyl ester
• 英文别名: 2-Diethoxyphosphoryl-4-methoxy-1-(2-phenylethynyl)benzene
• CAS: 639517-02-5
• 化学式: C₁₉H₂₁O₄P
• 分子量: 344.347
• InChiKey: NSRLLIKACSWYGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 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-methoxy-2-phenylethynyl-phenyl)-phosphonic acid diethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以87%的产率得到(5-methoxy-2-phenylethynylphenyl)phosphonic acid monoethyl ester
  参考文献：
  名称：

  Cu(I)催化邻乙炔苯基膦酸单酯分子内环化合成磷酸异香豆素

  摘要：

  研究了 Cu(I) 催化的邻乙炔基苯基膦酸单乙酯的分子内环化，并形成了一类新的六元磷杂环，具有高区域选择性和良好的产率。本反应是第一个将 P-OH 分子内加成到炔烃的例子，它为合成具有潜在生物活性的新型磷杂环提供了一种方便的方法。

  DOI：

  10.1021/ja038627f
• 作为产物：
  描述：

  2-(diethoxyphosphoryl)-4-methoxyphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (5-methoxy-2-phenylethynyl-phenyl)-phosphonic 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

• A convenient and applicable route to synthesize 2-(1-alkynyl)phenylphosphonates
  作者：Ai-Yun Peng、Xin-Ying Zhang、Yi-Xiang Ding

  DOI：10.1002/hc.20156

  日期：——

  A convenient and applicable route has been developed to synthesize various 2-(1-alkynyl)- phenylphosphonates starting from easily available phenols via palladium-catalyzed alkynyl-dehydroxylation of 2-hydroxylphenylphosphonates. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:529–534, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20156

  已经开发了一种方便且适用的路线，以通过钯催化的 2-羟基苯基膦酸酯的炔基脱羟基化，从容易获得的酚类开始合成各种 2-(1-炔基)-苯基膦酸酯。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:529–534, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20156
• The Synthesis of Phosphaisocoumarins by Cu(I)-Catalyzed Intramolecular Cyclization of <i>o</i>-Ethynylphenylphosphonic Acid Monoesters
  作者：Ai-Yun Peng、Yi-Xiang Ding

  DOI：10.1021/ja038627f

  日期：2003.12.1

  Cu(I)-catalyzed intramolecular cyclization of o-ethynylphenylphosphonic acid monoethyl esters was examined, and a new class of six-membered phosphorus heterocycles was formed with high regioselectivity and good yields. The present reaction is the first example of intramolecular addition of P-OH to alkynes, which provides a convenient way to synthesize novel phosphorus heterocycles having potential

  研究了 Cu(I) 催化的邻乙炔基苯基膦酸单乙酯的分子内环化，并形成了一类新的六元磷杂环，具有高区域选择性和良好的产率。本反应是第一个将 P-OH 分子内加成到炔烃的例子，它为合成具有潜在生物活性的新型磷杂环提供了一种方便的方法。
• Synthesis of 4-halophosphaisocoumarins via halocyclization of 2-(1-alkynyl)phenylphosphonates
  作者：Ai-Yun Peng、Yi-Xiang Ding

  DOI：10.1016/j.tet.2005.08.032

  日期：2005.10

  A series of 4-halophosphaisocoumarins were prepared with high regioselectivity in good to excellent yields under mild conditions by the reaction of 2-(1-alkynyl)phenylphosphonic acid diesters with I2 in CHCl3 or ICl in CH2Cl2, or by the reaction of 2-(1-alkynyl)phenylphosphonic acid monoesters with NBS or NCS in DMF. Whether the alkynylphosphonates could cyclize or not was affected by the substituents

  通过2-（1-炔基）苯基膦酸二酯与I 2在CHCl 3中或ICl在CH 2 Cl 2中的反应，或通过在2-（1-炔基）苯基膦酸单酯与NBS或NCS在DMF中的反应 炔基膦酸酯是否可以环化受取代基，反应溶剂和亲电试剂的影响。讨论了这种反应的原理。
• 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。
• An Efficient Route to 4-Halophosphaisocoumarins via CuX₂-Mediated Direct Halocyclization of 2-(1-Alkynyl)phenylphosphonic Acid Diesters
  作者：Ai-Yun Peng、Fei Hao、Baojian Li、Zheng Wang、Yidan Du

  DOI：10.1021/jo801842g

  日期：2008.11.21

  A series of 4-halophosphaisocoumarins were synthesized via CuX2 (X = Br, Cl) -mediated direct halocyclization of 2-(1-alkynyl)phenylphosphonic acid diesters in dichloroethane with the addition of n-Bu4NX or/and AgI in good to excellent yields. This reaction provides an efficient route to 4-halophosphaisocoumarins and represents the first example of bromo- and chlorocyclization of unsaturated phosphonic

  通过CuX2（X = Br，Cl）介导的2-（1-炔基）苯基膦酸二酯在二氯乙烷中的直接卤代环化反应，合成了一系列4-卤代磷酸异香豆素，并添加了n-Bu4NX或/和AgI，收率良好。 。该反应提供了通往4-卤代磷酸异香豆素的有效途径，并代表了不饱和膦酸二酯的溴环和氯环化的第一个实例。