(1S,4R)-6-fluoro-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one | 918452-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,4R)-6-fluoro-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one
• 英文别名: (1S,4R)-6-fluoro-2-[(4-methoxyphenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 918452-19-4
• 化学式: C₁₄H₁₄FNO₂
• 分子量: 247.269
• InChiKey: XUUKAVBTWHOLRD-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R)-6-fluoro-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one 在 盐酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (1R,4S)-4-amino-3-fluorocyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors

  摘要：

  On the basis of the structures of several potent inhibitor molecules for gamma-aminobutryric acid aminotransferase (GABA-AT) that were previously reported, six modified fluorine-containing conformationally restricted analogues were designed, synthesized, and tested as GABA-AT inhibitors. The syntheses of all six molecules followed from a readily synthesized ketone intermediate. Three of the molecules were found to be irreversible inhibitors of GABA-AT with comparable or larger k(inact)/K-I values than that of vigabatrin, a clinically used antiepilepsy drug, and the other three were reversible inhibitors. A possible mechanism for inactivation by one of the inactivators is proposed.

  DOI：

  10.1021/jm0608715
• 作为产物：
  描述：

  (1S,4R)-2-(4-methoxybenzyl)-6-trimethylstannanyl-2-azabicyclo[2.2.1]hept-5-en-3-one 在 2,6-二叔丁基-4-甲基吡啶 、 二氟代氙 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以30%的产率得到(1S,4R)-6-fluoro-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one
  参考文献：
  名称：

  Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors

  摘要：

  On the basis of the structures of several potent inhibitor molecules for gamma-aminobutryric acid aminotransferase (GABA-AT) that were previously reported, six modified fluorine-containing conformationally restricted analogues were designed, synthesized, and tested as GABA-AT inhibitors. The syntheses of all six molecules followed from a readily synthesized ketone intermediate. Three of the molecules were found to be irreversible inhibitors of GABA-AT with comparable or larger k(inact)/K-I values than that of vigabatrin, a clinically used antiepilepsy drug, and the other three were reversible inhibitors. A possible mechanism for inactivation by one of the inactivators is proposed.

  DOI：

  10.1021/jm0608715