(1aS,3aR,7aR)-Hexahydro-1-oxa-5-aza-cyclopropa[c]indene-5-carboxylic acid benzyl ester | 140211-14-9

• 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: (1aS,3aR,7aR)-Hexahydro-1-oxa-5-aza-cyclopropa[c]indene-5-carboxylic acid benzyl ester
• CAS: 140211-14-9
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: APOLBBMEXGQMKU-IJEWVQPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  42.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1aS,3aR,7aR)-Hexahydro-1-oxa-5-aza-cyclopropa[c]indene-5-carboxylic acid benzyl ester 在 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 0.08h， 以57%的产率得到benzyl (trans)-5-oxooctahydro-2H-cyclopenta[c]pyridine-2-carboxylate
  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：

  benzyl 3-allyl-4-oxo-piperidine-1-carboxylate 在 偶氮二异丁腈 、 potassium tert-butylate 、 triethyloxonium fluoroborate 作用下， 反应 20.5h， 生成 (1aS,3aR,7aR)-Hexahydro-1-oxa-5-aza-cyclopropa[c]indene-5-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