methyl 5-(2-methoxyethoxy)nicotinate | 874285-28-6

• 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: methyl 5-(2-methoxyethoxy)nicotinate
• 英文别名: Methyl 5-(2-methoxyethoxy)pyridine-3-carboxylate
• CAS: 874285-28-6
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: VRFPFXJAOOGALR-UHFFFAOYSA-N

物化性质

• 沸点：
  313.6±32.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-methoxyethoxy)nicotinate 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以76%的产率得到methyl 5-(2-methoxyethoxy)pyridine-3-carboxylate 1-oxide
  参考文献：
  名称：

  An Efficient, Regioselective Amination of 3,5-Disubstituted Pyridine N-Oxides Using Saccharin as an Ammonium Surrogate

  摘要：

  A process for the regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides has been developed utilizing cheap, readily available saccharin as an ammonium surrogate. High conversions of the corresponding saccharin adducts have been achieved under mild reaction conditions. In situ deprotection under acidic conditions allows for a one-pot process to substituted aminopyridines. High regioselectivities were obtained from a variety of 3,5-disubstituted pyridine N-oxides.

  DOI：

  10.1021/ol303218p
• 作为产物：
  描述：

  2-氯乙基甲基醚 、 5-羟基烟酸甲酯 在 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以76%的产率得到methyl 5-(2-methoxyethoxy)nicotinate
  参考文献：
  名称：

  An Efficient, Regioselective Amination of 3,5-Disubstituted Pyridine N-Oxides Using Saccharin as an Ammonium Surrogate

  摘要：

  A process for the regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides has been developed utilizing cheap, readily available saccharin as an ammonium surrogate. High conversions of the corresponding saccharin adducts have been achieved under mild reaction conditions. In situ deprotection under acidic conditions allows for a one-pot process to substituted aminopyridines. High regioselectivities were obtained from a variety of 3,5-disubstituted pyridine N-oxides.

  DOI：

  10.1021/ol303218p

文献信息

• Structure-Based Design of a Potent, Selective, and Brain Penetrating PDE2 Inhibitor with Demonstrated Target Engagement
  作者：Peter Buijnsters、Meri De Angelis、Xavier Langlois、Frederik J. R. Rombouts、Wendy Sanderson、Gary Tresadern、Alison Ritchie、Andrés A. Trabanco、Greet VanHoof、Yves Van Roosbroeck、José-Ignacio Andrés

  DOI：10.1021/ml500262u

  日期：2014.9.11

  Structure-guided design led to the identification of the novel, potent, and selective phosphodiesterase 2 (PDE2) inhibitor 12. Compound 12 demonstrated a >210-fold selectivity versus PDE10 and PDE11 and was inactive against all other PDE family members up to 10 mu M. In vivo evaluation of 12 provided evidence that it is able to engage the target and to increase cGMP levels in relevant brain regions. Hence, 12 is a valuable tool compound for the better understanding of the role of PDE2 in cognitive impairment and other central nervous system related disorders.