(3aS,4R,6aR)-4-Chloro-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester | 140211-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aS,4R,6aR)-4-Chloro-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester
• CAS: 140211-03-6
• 化学式: C₁₅H₁₈ClNO₂
• 分子量: 279.766
• InChiKey: GFHQSJCRADFGAR-BFHYXJOUSA-N

物化性质

• 沸点：
  411.3±38.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR)-4-Chloro-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 氰化钠 、 双氧水 作用下， 以 六甲基磷酰三胺 、 二甲基亚砜 为溶剂， 反应 8.5h， 生成 4-hydroxy-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester
  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：

  (3aS,6aR)-benzyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 在 四氯化碳 、 L-Selectride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (3aS,4R,6aR)-4-Chloro-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester
  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