N-Methyl-N-(3aS,4S,7aR)-octahydro-isoindol-4-yl-formamide; compound with trifluoro-acetic acid | 130657-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: N-Methyl-N-(3aS,4S,7aR)-octahydro-isoindol-4-yl-formamide; compound with trifluoro-acetic acid
• CAS: 130657-67-9
• 化学式: C₂HF₃O₂*C₁₀H₁₈N₂O
• 分子量: 296.29
• InChiKey: MKHKBQJZYTZUPZ-JYNKJOSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.64
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢喹啉-3-羧酸 、 N-Methyl-N-(3aS,4S,7aR)-octahydro-isoindol-4-yl-formamide; compound with trifluoro-acetic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 1-Cyclopropyl-6,8-difluoro-7-[(3aR,4R,7aS)-4-(formyl-methyl-amino)-octahydro-isoindol-2-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acids

  摘要：

  A series of novel 7-[amino-substituted azabicycloalkanyl]-6-fluoro-1-substituted quinolinecarboxylic acids (18-53) have been prepared and their antibacterial activities evaluated. These compounds are characterized structurally by a new amino-substituted azabicyclo[3.3.0]octane,-[4.3.0]nonane and -[5.3.0]decane ring systems at the 7-position of quinolonecarboxylic acids. To compare the biological activities of enantiomers, (+)-7[(1S, 5R)- and (-)-7[(1R, 5S)-1-aminomethyl-3-azabicyclo[3.3.0]-octan-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylic acid hydrochloride (43, 44) were synthesized and evaluated for antibacterial activity. Compound 43 was more potent than 44 against both Gram-positive and Gram-negative organisms. The structure-activity relationships of these quinolonecarboxylic acids are also discussed.

  DOI：

  10.1016/0223-5234(91)90131-6
• 作为产物：
  描述：

  在 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 N-Methyl-N-(3aS,4S,7aR)-octahydro-isoindol-4-yl-formamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of new 7-(aminoazabicycloalkanyl)quinolonecarboxylic acids

  摘要：

  A series of novel 7-[amino-substituted azabicycloalkanyl]-6-fluoro-1-substituted quinolinecarboxylic acids (18-53) have been prepared and their antibacterial activities evaluated. These compounds are characterized structurally by a new amino-substituted azabicyclo[3.3.0]octane,-[4.3.0]nonane and -[5.3.0]decane ring systems at the 7-position of quinolonecarboxylic acids. To compare the biological activities of enantiomers, (+)-7[(1S, 5R)- and (-)-7[(1R, 5S)-1-aminomethyl-3-azabicyclo[3.3.0]-octan-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolonecarboxylic acid hydrochloride (43, 44) were synthesized and evaluated for antibacterial activity. Compound 43 was more potent than 44 against both Gram-positive and Gram-negative organisms. The structure-activity relationships of these quinolonecarboxylic acids are also discussed.

  DOI：

  10.1016/0223-5234(91)90131-6