(5R)-5-[(E)-3-oxooct-1-enyl]-1-[2-tri(propan-2-yl)silyloxyethyl]pyrrolidin-2-one | 819067-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5R)-5-[(E)-3-oxooct-1-enyl]-1-[2-tri(propan-2-yl)silyloxyethyl]pyrrolidin-2-one
• CAS: 819067-22-6
• 化学式: C₂₃H₄₃NO₃Si
• 分子量: 409.685
• InChiKey: WORQAKYUAQJWSA-OSJHKOOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-5-[(E)-3-oxooct-1-enyl]-1-[2-tri(propan-2-yl)silyloxyethyl]pyrrolidin-2-one 在 dimethyl sulfide borane 、 potassium tert-butylate 、 四丁基氟化铵 、 三乙胺 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.75h， 生成 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester
  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：

  (2-bromoethoxy)triisopropylsilane 在 4-甲基苯磺酸吡啶 、 sodium hydride 、 N,N-二异丙基乙胺 、 potassium iodide 、 lithium chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.33h， 生成 (5R)-5-[(E)-3-oxooct-1-enyl]-1-[2-tri(propan-2-yl)silyloxyethyl]pyrrolidin-2-one
  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

文献信息

• Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of <i>N</i>-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents
  作者：Todd R. Elworthy、Emma R. Brill、San-San Chiou、Frances Chu、Jason R. Harris、R. Than Hendricks、Jane Huang、Woongki Kim、Leang K. Lach、Tara Mirzadegan、Calvin Yee、Keith A. M. Walker

  DOI：10.1021/jm049290a

  日期：2004.12.1

  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.