[hydroxy(pyridin-2-yl)methyl]phosphonic acid | 183016-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [hydroxy(pyridin-2-yl)methyl]phosphonic acid
• 英文别名: hydroxy(2-pyridyl)methylphosphonic acid
• CAS: 183016-66-2
• 化学式: C₆H₈NO₄P
• mdl: MFCD29971693
• 分子量: 189.108
• InChiKey: YSMGCYDOGVFHTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc(II) sulfate heptahydrate 、 [hydroxy(pyridin-2-yl)methyl]phosphonic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 以57%的产率得到[Zn7(hydroxy(2-pyridyl)methylphosphonate)6(H2O)6]SO4*4H2O
  参考文献：
  名称：

  [Zn₇{(2-C₅H₄N)CH(OH)PO₃}₆(H₂O)₆]SO₄·4H₂O:  A Zinc Phosphonate Cluster with a Drum-like Cage Structure

  摘要：

  Direct reaction of hydroxy(2-pyridyl)methylphosphonic acid with zinc sulfate under hydrothermal conditions results in the formation of the novel heptanuclear cluster compound [Zn-7{(2-C5H4N)CH(OH)PO3}(6)(H2O)(6)]SO4 center dot 4H(2)O (1). The inorganic core of the cluster can be described as a cylindrical drum made up of six Zn atoms bridged by six {CPO3} units that is centered by a seventh Zn atom. Crystal data: monoclinic, C2/c, a = 22.690(2) angstrom, b = 16.675(2) angstrom, c 18.151(2) angstrom, beta = 93.390(2)degrees.

  DOI：

  10.1021/ic0500659
• 作为产物：
  描述：

  diethyl 1-hydroxy-1-(pyridin-2’-yl)methyl phosphonate 在 盐酸 作用下， 反应 6.0h， 以58%的产率得到[hydroxy(pyridin-2-yl)methyl]phosphonic acid
  参考文献：
  名称：

  吡啶基甲基（氨基）膦酸酯的酸性裂解。形成相应的胺

  摘要：

  3-吡啶基甲基（氨基）膦酸酯的水解通过20％aq。水溶液进行。如所预期的，盐酸得到相应的3-吡啶基甲基（氨基）膦酸。然而，2-和4-吡啶基甲基（氨基）膦酸酯的水解导致膦酸酯的分解，具有CP键的裂解并形成相应的胺。剩余的磷部分被鉴定为磷酸。反应范围限于氨基膦酸的2-和4-吡啶基甲基衍生物及其酯，以及具有相似结构的衍生物。相反，2-和4-吡啶基甲基（氨基）膦酸酯的碱性水解产生相应的氨基膦酸酯单烷基酯，在这些情况下未观察到CP键的断裂。

  DOI：

  10.1016/0040-4020(96)00727-2

文献信息

• Novel hydroxyphosphonate inhibitors of CD-45 tyrosine phosphatase
  作者：Roger F. Frechette、Caridad Ackerman、Scott Beers、Rich Look、John Moore

  DOI：10.1016/s0960-894x(97)00390-9

  日期：1997.9

  CD-45 tyrosine phosphatase [E.C. 3.1.3.48] is an important player in the regulation of cell activation and proliferation in hematopoetic cells. As part of a program in immune response modulation, we prepared the first series of small organic molecule inhibitors of CD-45. The preparation and in vitro screening of these hydroxyphosphonates is described herein. (C) 1997 Elsevier Science Ltd.
• The acidic cleavage of pyridylmethyl(amino)phosphonates. Formation of the corresponding amines
  作者：Bogdan Boduszek

  DOI：10.1016/0040-4020(96)00727-2

  日期：1996.9

  Hydrolysis of 3-pyridylmethyl(amino)phosphonates by means of 20% aq. hydrochloric acid gave corresponding 3-pyridylmethyl(amino)phosphonic acids, as expected. However, hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to decomposition of the phosphonates with a cleavage of CP bond and formation of the corresponding amines. The leaving phosphorus moiety was identified as phosphoric acid.

  3-吡啶基甲基（氨基）膦酸酯的水解通过20％aq。水溶液进行。如所预期的，盐酸得到相应的3-吡啶基甲基（氨基）膦酸。然而，2-和4-吡啶基甲基（氨基）膦酸酯的水解导致膦酸酯的分解，具有CP键的裂解并形成相应的胺。剩余的磷部分被鉴定为磷酸。反应范围限于氨基膦酸的2-和4-吡啶基甲基衍生物及其酯，以及具有相似结构的衍生物。相反，2-和4-吡啶基甲基（氨基）膦酸酯的碱性水解产生相应的氨基膦酸酯单烷基酯，在这些情况下未观察到CP键的断裂。
• [Zn₇{(2-C₅H₄N)CH(OH)PO₃}₆(H₂O)₆]SO₄·4H₂O:  A Zinc Phosphonate Cluster with a Drum-like Cage Structure
  作者：Deng-Ke Cao、Yi-Zhi Li、Li-Min Zheng

  DOI：10.1021/ic0500659

  日期：2005.5.1

  Direct reaction of hydroxy(2-pyridyl)methylphosphonic acid with zinc sulfate under hydrothermal conditions results in the formation of the novel heptanuclear cluster compound [Zn-7(2-C5H4N)CH(OH)PO3}(6)(H2O)(6)]SO4 center dot 4H(2)O (1). The inorganic core of the cluster can be described as a cylindrical drum made up of six Zn atoms bridged by six CPO3} units that is centered by a seventh Zn atom. Crystal data: monoclinic, C2/c, a = 22.690(2) angstrom, b = 16.675(2) angstrom, c 18.151(2) angstrom, beta = 93.390(2)degrees.