diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate | 204130-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate
• 英文别名: 2-[Diethoxyphosphoryl(hydroxy)methyl]-4-nitrophenol
• CAS: 204130-59-6
• 化学式: C₁₁H₁₆NO₇P
• 分子量: 305.224
• InChiKey: GBEIXGOTZXPEGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 (2-Hydroxy-5-nitro)phenylhydroxymethylphosphonic acid
  参考文献：
  名称：

  Novel hydroxyphosphonate inhibitors of CD-45 tyrosine phosphatase

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)00390-9
• 作为产物：
  描述：

  5-硝基水杨醛 、 亚磷酸二乙酯 在 phosphosulfonic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.58h， 以89%的产率得到diethyl (hydroxy(2-hydroxy-5-nitrophenyl)methyl)phosphonate
  参考文献：
  名称：

  Phospho sulfonic acid: an efficient and recyclable solid acid catalyst for the solvent-free synthesis of α-hydroxyphosphonates and their anticancer properties

  摘要：

  一些由绿色合成方法合成的化合物显示出强大的抗癌活性。

  DOI：

  10.1039/c5nj00312a

文献信息

• Nitroarylhydroxymethylphosphonic acids as inhibitors of CD45
  作者：Scott A. Beers、Elizabeth A. Malloy、Wei Wu、Michael P. Wachter、Uma Gunnia、Druie Cavender、Crafford Harris、Janet Davis、Ruth Brosius、J.Lee Pellegrino-Gensey、John Siekierka

  DOI：10.1016/s0968-0896(97)00174-0

  日期：1997.12

  A series of nitroarylhydroxymethylphosphonic acids was synthesized and evaluated as inhibitors of CD45. It was discovered that both the alpha hydroxy and nitro groups are essential for activity. Potency is enhanced by the addition of a large lipophilic group on the aryl ring adjacent to the phosphonic acid moiety. Kinetics studies have shown that these compounds are competitive inhibitors and thus bind at the active site of this enzyme. (C) 1997 Elsevier Science Ltd.