diethyl hexyloxy(naphthalen-1-yl)methylphosphonate | 1123189-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl hexyloxy(naphthalen-1-yl)methylphosphonate
• CAS: 1123189-30-9
• 化学式: C₂₁H₃₁O₄P
• 分子量: 378.448
• InChiKey: BXQYETWUPKGVAP-UHFFFAOYSA-N

物化性质

• 沸点：
  486.6±38.0 °C(predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diethyl hexyloxy(naphthalen-1-yl)methylphosphonate 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以89%的产率得到hexyloxy(naphthalen-1-yl)methylphosphonic acid
  参考文献：
  名称：

  Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids

  摘要：

  Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The K(i) values of these compounds are as low as 4 mu M, the lowest reported to date for a PAP inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.125
• 作为产物：
  描述：

  (diethoxyphosphoryl)(naphthalen-1-yl)methyl methanesulfonate 、 正己醇 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以68%的产率得到diethyl hexyloxy(naphthalen-1-yl)methylphosphonate
  参考文献：
  名称：

  Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids

  摘要：

  Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The K(i) values of these compounds are as low as 4 mu M, the lowest reported to date for a PAP inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.125