1-ethoxy-7-methoxy-3-phenylbenzo[c][1,2]oxaphosphinine 1-oxide | 639517-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-ethoxy-7-methoxy-3-phenylbenzo[c][1,2]oxaphosphinine 1-oxide
• 英文别名: 1-Ethoxy-7-methoxy-3-phenyl-2,1lambda5-benzoxaphosphinine 1-oxide；1-ethoxy-7-methoxy-3-phenyl-2,1λ5-benzoxaphosphinine 1-oxide
• CAS: 639517-26-3
• 化学式: C₁₇H₁₇O₄P
• 分子量: 316.293
• InChiKey: ZFYYOUZYMRBJIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-ethoxy-7-methoxy-3-phenylbenzo[c][1,2]oxaphosphinine 1-oxide 在 三甲基溴硅烷 、 sodium iodide 、 甲醇 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以92%的产率得到1-hydroxy-7-methoxy-3-phenylbenzo[c][1,2]oxaphosphinine 1-oxide
  参考文献：
  名称：

  Synthesis of Phosphaisocoumarin Acids via Me3SiX-Mediated Dealkylation Reaction

  摘要：

  在不同条件下研究了磷酸异香豆素酯的脱烷基化。通过磷酸异香豆素酯与 Me3SiBr 在氯仿中反应，然后用甲醇处理，或在乙腈中与 Me3SiCl 和 NaI 反应，然后水解，开发了一种合成磷酸异香豆素酸的有效方法，在温和条件下具有良好至优异的产率。

  DOI：

  10.1055/s-2008-1067187
• 作为产物：
  描述：

  1-ethoxy-7-methoxy-3-phenyl-4-iodobenzo[c][1,2]oxaphosphinine 1-oxide 在 bis-triphenylphosphine-palladium(II) chloride 甲酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-ethoxy-7-methoxy-3-phenylbenzo[c][1,2]oxaphosphinine 1-oxide
  参考文献：
  名称：

  Synthesis of Phosphaisocoumarins via Iodocyclization

  摘要：

  4-lodophosphaisocoumarins can be prepared in good yield and with high regioselectivity under mild conditions by the reaction of o-(1-alkynyl)phenylphosphonates with I-2 or ICI. The present reaction represents the first example of a phosphonate iodocyclization onto a C-C triple bond. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.

  DOI：

  10.1021/ol0499506

文献信息

• 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。
• Acid/base-catalyzed cyclization of O-alkynylphenylphosphonic acid monoesters and (O-hydroxyphenyl)ethynylphosphinates
  作者：Ai-Yun Peng、Yidan Du、Yingling Wei、Liang Xie、Yi-Xiang Ding

  DOI：10.1002/hc.20728

  日期：2011.9

  In this work, we found that acids (i.e., HCl and NaHSO3) rather than bases could catalyze the cyclization of o-alkynylphenylphosphonic acid monoesters at slow rates and give phosphaisocoumarins in low to medium yields, whereas the cyclization of (o-hydroxyphenyl)ethynylphosphinates proceeded very smoothly under basic conditions rather than acidic conditions, and a series of phosphachromones could be

  在这项工作中，我们发现酸（即 HCl 和 NaHSO3）而不是碱可以以缓慢的速率催化邻炔基苯基膦酸单酯的环化，并以低到中等的收率产生磷酸异香豆素，而（邻羟基苯基）乙炔基次膦酸酯的环化在碱性条件下而不是酸性条件下进行非常顺利，并且在室温下使用 K2CO3 作为催化剂可以以优异的产率制备一系列磷色酮。这是通过酸/碱催化的炔烃分子内环化合成磷杂环的第一个例子。讨论了可能的机制。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:649–652, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20728
• Synthesis of phosphaisocoumarin amidates via DIBAL-H-mediated selective amidation of phosphaisocoumarin esters
  作者：Yu-Juan Guo、Pei-Jiang Chen、Bo Wang、Ai-Yun Peng

  DOI：10.1039/c4ob00663a

  日期：——

  A series of phosphaisocoumarin amidates were synthesized via DIBAL-H-mediated selective amidation of phosphaisocoumarin esters in good to excellent yields. In each case, the phostone ring was intact and only the exocyclic ethoxy group was amidated.

  一系列磷异香豆素酯酰胺化合物被成功地合成，通过DIBAL-H介导的选择性酰化反应，产率良好至优良。在每种情况下，磷酸酯环保持完整，只有外环乙氧基被酰化。
• Alcoholysis of Phosphaisocoumarins and Synthesis of 2-(2-Oxoalkyl)phenylphosphonates
  作者：Ai-Yun Peng、Yu-Juan Guo、Zhi-Hai Ke、Shizheng Zhu

  DOI：10.1002/ejoc.200800616

  日期：2008.11

  4-bromophosphaisocoumarins underwent a dehalogenation–alcoholysis tandem reaction. The possible mechanism for the alcoholysis reaction was discussed. In addition, direct access to 2-(2-oxoalkyl)phenylphosphonates was developed by the mercury(II)-catalyzed hydration of 2-(1-alkynly)phenylphosphonates with high regioselectivity. In a preliminary study, the obtained novel keto phosphonates showed medium inhibitory

  磷酸异香豆素不发生氨解，但发现它们在醇和伯胺的存在下对醇解敏感。本文研究了这种意想不到的醇解反应，发现在 Et3N 或 K2CO3 存在下，4-未取代和 4-氯代磷杂香豆素顺利进行醇解反应，以良好的收率得到一系列 2-(2-氧代烷基)苯基膦酸酯，而 4 -碘-和4-溴磷异香豆素经历了脱卤-醇解串联反应。讨论了醇解反应的可能机理。此外，通过汞（II）催化的具有高区域选择性的 2-（1-炔基）苯基膦酸酯的水合开发了直接获得 2-（2-氧代烷基）苯基膦酸酯的方法。在初步研究中，获得的新型酮膦酸盐对α-胰凝乳蛋白酶显示中等抑制活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• 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.