(1S,4R)-6-methylenyl-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one | 640896-91-9

• 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: (1S,4R)-6-methylenyl-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one
• 英文别名: (1S,4S)-2-benzyl-6-methylidene-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 640896-91-9
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: UFLUMCWJGPSZFY-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,4R)-6-methylenyl-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one 在 盐酸 、 氨 、 sodium 、 溶剂黄146 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 5.23h， 生成 (1S,3S)-3-amino-4-methylenyl-1-cyclopentanoic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor

  摘要：

  Previously it was found that a conformationally rigid analogue (2) of the epilepsy drug vigabatrin (1) did not inactivate gamma-aminobutyric acid aminotransferase (GABA-AT), A cyclic compound with an exocyclic double bond (6) was synthesized and was found to inactivate GABA-AT, but only in the absence of 2-mereaptoethanol. The corresponding difluoro-substituted analogue (14) was synthesized and was shown to be a very potent time-dependent inhibitor, even in the presence of 2-mercaptoethanol.

  DOI：

  10.1021/jm034162s
• 作为产物：
  描述：

  (1S,4R)-6-exo-trimethylsilylmethyl-6-endo-hydroxy-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one 在 4-二甲氨基吡啶 、 三氟乙酸酐 、 potassium fluoride 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以86%的产率得到(1S,4R)-6-methylenyl-2-benzyl-2-azabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor

  摘要：

  Previously it was found that a conformationally rigid analogue (2) of the epilepsy drug vigabatrin (1) did not inactivate gamma-aminobutyric acid aminotransferase (GABA-AT), A cyclic compound with an exocyclic double bond (6) was synthesized and was found to inactivate GABA-AT, but only in the absence of 2-mereaptoethanol. The corresponding difluoro-substituted analogue (14) was synthesized and was shown to be a very potent time-dependent inhibitor, even in the presence of 2-mercaptoethanol.

  DOI：

  10.1021/jm034162s

文献信息

• Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor
  作者：Yue Pan、Jian Qiu、Richard B. Silverman

  DOI：10.1021/jm034162s

  日期：2003.12.1

  Previously it was found that a conformationally rigid analogue (2) of the epilepsy drug vigabatrin (1) did not inactivate gamma-aminobutyric acid aminotransferase (GABA-AT), A cyclic compound with an exocyclic double bond (6) was synthesized and was found to inactivate GABA-AT, but only in the absence of 2-mereaptoethanol. The corresponding difluoro-substituted analogue (14) was synthesized and was shown to be a very potent time-dependent inhibitor, even in the presence of 2-mercaptoethanol.