Phenylmethyl (2R,4R)-4-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-5-hydroxy-2,4-diphenyl-3-oxazolidinecarboxylate | 1160593-48-5

• 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: Phenylmethyl (2R,4R)-4-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-5-hydroxy-2,4-diphenyl-3-oxazolidinecarboxylate
• 英文别名: benzyl (2R,4R)-4-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-5-hydroxy-2,4-diphenyl-1,3-oxazolidine-3-carboxylate
• CAS: 1160593-48-5
• 化学式: C₃₄H₂₉F₆NO₅
• 分子量: 645.598
• InChiKey: GVQJXOMRECYGJZ-WGMUOYJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Phenylmethyl (2R,4R)-4-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-5-hydroxy-2,4-diphenyl-3-oxazolidinecarboxylate 在 platinum(IV) oxide 、 nitronium tetrafluoborate 、 氢气 、 双(三甲基硅烷基)氨基钾 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 作用下， 生成
  参考文献：
  名称：

  Conformation of gem-disubstituted alkylarylpiperidines and their implication in design and synthesis of a conformationally-rigidified NK1 antagonist

  摘要：

  Piperidines are ubiquitous in pharmaceuticals and bioactive natural products. Understanding the structural and functional properties of piperidines plays a key role in drug design and development. This Letter reported studies of conformation of a set of gem-disubstituted methylphenylpiperidines in the context of discovery of NK1 antagonists. The findings led to re-design and an efficient synthesis of a potent NK1 antagonist with excellent in vivo activity and rodent and monkey pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.131
• 作为产物：
  描述：

  罗拉吡坦中间体 在 锂硼氢 、 lithium diisopropyl amide 作用下， 生成 Phenylmethyl (2R,4R)-4-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-5-hydroxy-2,4-diphenyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  Conformation of gem-disubstituted alkylarylpiperidines and their implication in design and synthesis of a conformationally-rigidified NK1 antagonist

  摘要：

  Piperidines are ubiquitous in pharmaceuticals and bioactive natural products. Understanding the structural and functional properties of piperidines plays a key role in drug design and development. This Letter reported studies of conformation of a set of gem-disubstituted methylphenylpiperidines in the context of discovery of NK1 antagonists. The findings led to re-design and an efficient synthesis of a potent NK1 antagonist with excellent in vivo activity and rodent and monkey pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.131