ethyl 4-[2-[[(4S)-4-hydroxy-5-phenylmethoxypentanoyl]amino]ethyl]benzoate | 493036-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-[2-[[(4S)-4-hydroxy-5-phenylmethoxypentanoyl]amino]ethyl]benzoate
• CAS: 493036-25-2
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: YCQLJGABCWHFCV-NRFANRHFSA-N

物化性质

• 沸点：
  614.5±55.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-[2-[[(4S)-4-hydroxy-5-phenylmethoxypentanoyl]amino]ethyl]benzoate 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 (R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-hydroxymethyl-2-pyrrolidinone
  参考文献：
  名称：

  Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of N-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents

  摘要：

  Two distinct synthetic schemes were applied to access heteroatom-containing alpha-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. gamma-Lactams were characterized for their prostanoid EP receptor affinities and EP4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.

  DOI：

  10.1021/jm049290a
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 1,5-二氮杂双环[4.3.0]壬-5-烯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 ethyl 4-[2-[[(4S)-4-hydroxy-5-phenylmethoxypentanoyl]amino]ethyl]benzoate
  参考文献：
  名称：

  Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of N-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents

  摘要：

  Two distinct synthetic schemes were applied to access heteroatom-containing alpha-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. gamma-Lactams were characterized for their prostanoid EP receptor affinities and EP4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.

  DOI：

  10.1021/jm049290a