(E)-(1S,4S)-2-(4-methoxybenzyl)-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-3-one | 918452-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-(1S,4S)-2-(4-methoxybenzyl)-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-3-one
• 英文别名: (1S,4S,6E)-2-[(4-methoxyphenyl)methyl]-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 918452-34-3
• 化学式: C₁₆H₁₆F₃NO₂
• 分子量: 311.304
• InChiKey: GRSCDKZLJTUHNT-QSMMMUJJSA-N

物化性质

• 沸点：
  457.9±45.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(1S,4S)-2-(4-methoxybenzyl)-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-3-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以74%的产率得到(E)-(1S,4S)-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-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
• 作为产物：
  描述：

  (1S,4R)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3,6-dione 在 六甲基磷酰三胺 、 copper(l) iodide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (E)-(1S,4S)-2-(4-methoxybenzyl)-6-(2,2,2-trifluoroethylidene)-2-azabicyclo[2.2.1]heptan-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

文献信息

• Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors
  作者：Hejun Lu、Richard B. Silverman

  DOI：10.1021/jm0608715

  日期：2006.12.1

  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.