5-(2-Hydroxyethyl)-1,3-dimethylpyridin-2-one | 380228-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(2-Hydroxyethyl)-1,3-dimethylpyridin-2-one
• CAS: 380228-00-2
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: KGPBTQRRYNKOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-Hydroxyethyl)-1,3-dimethylpyridin-2-one 在 正丙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 生成 5-(2-{(S)-2-[5-[2-(2-Aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-propylamino}-ethyl)-1,3-dimethyl-1H-pyridin-2-one
  参考文献：
  名称：

  Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity

  摘要：

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00512-1
• 作为产物：
  描述：

  2-羟基-3-甲基-5-溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 palladium on activated charcoal 、 N-溴代丁二酰亚胺(NBS) 、 水 、 ammonium formate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(2-Hydroxyethyl)-1,3-dimethylpyridin-2-one
  参考文献：
  名称：

  Orally bioavailable, indole-based nonpeptide GnRH receptor antagonists with high potency and functional activity

  摘要：

  Stereospecific introduction of a methyl group to the indole-3-side chain enhanced activity in our tryptamine-derived series of GnRH receptor antagonists. Further improvements were achieved by variation of the bicyclic amino moiety of the tertiary amide and by adjustment of the tether length to a pyridine or pyridone terminus. These modifications culminated in analogue 24, which had oral activity in a rat model and acceptable oral bioavailability and half-life in dogs and monkeys. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00512-1