(3aS,7aR)-4-Oxo-octahydro-isoindole-2-carboxylic acid benzyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3aS,7aR)-4-Oxo-octahydro-isoindole-2-carboxylic acid benzyl ester
• 英文别名: benzyl (3aR,7aS)-7-oxo-3,3a,4,5,6,7a-hexahydro-1H-isoindole-2-carboxylate
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: HBZMLXFYUNKDHL-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,7aR)-4-Oxo-octahydro-isoindole-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (3aR,7aS)-spiro[1,2,3,3a,4,5,6,7a-octahydroisoindole-7,2'-1,3-dioxolane]
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position

  摘要：

  A series of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position were synthesized to obtain potent drugs for the treatment of Gram-positive infections. Some compounds exhibited excellent antibacterial activity, and potent inhibitory activity against bacterial DNA topoisomerase IV. In addition, some of the potent compounds showed reduced inhibitory activity against human DNA topoisomerase II compared with the corresponding noncyclopropane-fused compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.064
• 作为产物：
  描述：

  2-环己烯-1-酮 在 sodium carbonate 、 三氟乙酸 作用下， 以 水 、 甲苯 为溶剂， 反应 64.58h， 生成 (3aS,7aR)-4-Oxo-octahydro-isoindole-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