(2S,4R)-N-(4-tolylsulfonyl)-2-methyl-4-<(4-tolylsulfonyl)oxy>pyrrolidine | 144043-29-8

• 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: (2S,4R)-N-(4-tolylsulfonyl)-2-methyl-4-<(4-tolylsulfonyl)oxy>pyrrolidine
• 英文别名: (2S,4R)-N-(4-tolylsulfonyl)-2-methyl-4-[(4-tolylsulfonyl)oxy]pyrrolidine；[(3R,5S)-5-methyl-1-(4-methylphenyl)sulfonylpyrrolidin-3-yl] 4-methylbenzenesulfonate
• CAS: 144043-29-8；144043-30-1
• 化学式: C₁₉H₂₃NO₅S₂
• 分子量: 409.527
• InChiKey: GOOICMAMFZNYMQ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  97.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N-(4-tolylsulfonyl)-2-methyl-4-<(4-tolylsulfonyl)oxy>pyrrolidine 在 palladium on activated charcoal sodium azide 、 氢溴酸 、 氢气 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.67h， 生成 7-((2S,4S)-4-Amino-2-methyl-pyrrolidin-1-yl)-1-tert-butyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028
• 作为产物：
  描述：

  (2R,4R)-4-hydroxy-2-hydroxymethyl-1-(4-tolylsulfonyl)pyrrolidine 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 (2S,4R)-N-(4-tolylsulfonyl)-2-methyl-4-<(4-tolylsulfonyl)oxy>pyrrolidine
  参考文献：
  名称：

  Fluoronaphthyridines and -quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral 1-tert-butyl-6-fluoro-7-substituted-naphthyridones

  摘要：

  A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared. These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position. In this paper we report the full details of the asymmetric synthesis of this series of compounds. Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity. Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

  DOI：

  10.1021/jm00100a028