Z-(1S,4S)-6-fluoromethylenyl-2-azabicyclo[2.2.1]heptan-3-one | 757942-78-2

• 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: Z-(1S,4S)-6-fluoromethylenyl-2-azabicyclo[2.2.1]heptan-3-one
• 英文别名: (Z)-(1S,4S)-6-fluoromethylenyl-2-azabicyclo[2.2.2]heptan-3-one；(1S,4S,6Z)-6-(fluoromethylidene)-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 757942-78-2
• 化学式: C₇H₈FNO
• 分子量: 141.145
• InChiKey: JKKPGUUMDAUSMB-WREUKLMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Z-(1S,4S)-6-fluoromethylenyl-2-azabicyclo[2.2.1]heptan-3-one 在 盐酸 作用下， 反应 10.0h， 以75%的产率得到Z-(1S,SS)-3-amino-4-fluoromethylenyl-1-cyclopentanoic acid hydrochloride
  参考文献：
  名称：

  Conformationally-restricted vigabatrin analogs as irreversible and reversible inhibitors of γ-aminobutyric acid aminotransferase

  摘要：

  Compounds that inhibit gamma-aminobutyric acid aminotransferase exhibit anticonvulsant activity; vigabatrin is a known irreversible inhibitor of this enzyme and anticonvulsant drug. Conformationally-restricted, five-membered- and six-membered-ring vigabatrin analogs were synthesized and tested as inhibitors of gamma-aminobutyric acid aminotransferase. Two monofluorinated compounds, 4 and 5, are time-dependent inhibitors of the enzyme, and their potencies are comparable to that of vigabatrin. Compounds 6 and 7 are weak reversible inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.065
• 作为产物：
  描述：

  (E/Z)-(1S,4S)-6-(1‘-fluoro-1‘-phenylsulfonyl)methylenyl-2-(4‘-methoxybenzyl)-2-azabicyclo[2.2.2]heptan-3-one 在 ammonium cerium(IV) nitrate 、 magnesium 、 mercury dichloride 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 Z-(1S,4S)-6-fluoromethylenyl-2-azabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Conformationally-restricted vigabatrin analogs as irreversible and reversible inhibitors of γ-aminobutyric acid aminotransferase

  摘要：

  Compounds that inhibit gamma-aminobutyric acid aminotransferase exhibit anticonvulsant activity; vigabatrin is a known irreversible inhibitor of this enzyme and anticonvulsant drug. Conformationally-restricted, five-membered- and six-membered-ring vigabatrin analogs were synthesized and tested as inhibitors of gamma-aminobutyric acid aminotransferase. Two monofluorinated compounds, 4 and 5, are time-dependent inhibitors of the enzyme, and their potencies are comparable to that of vigabatrin. Compounds 6 and 7 are weak reversible inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.065