[(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-(2-methoxy-ethyl)-carbamic acid benzyl ester | 909396-01-6

• 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: [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-(2-methoxy-ethyl)-carbamic acid benzyl ester
• CAS: 909396-01-6
• 化学式: C₃₂H₃₂F₇NO₄
• 分子量: 627.599
• InChiKey: CVUDEFAFLKSNOC-FKTIWSFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-(2-methoxy-ethyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-(2-methoxy-ethyl)-amine
  参考文献：
  名称：

  Cyclopentane-based human NK1 antagonists. Part 2: Development of potent, orally active, water-soluble derivatives

  摘要：

  The synthesis and optimization of a cyclopentane-based hNK1 antagonist scaffold 3, having four chiral centers, will be discussed in the context of its enhanced water-solubility properties relative to the marketed anti-emetic hNK1 antagonist EMEND (R) (Aprepitant). Sub-nanomolar hNK1 binding was achieved and oral activity comparable to Aprepitant in two in vivo models will be described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.044
• 作为产物：
  描述：

  methyl (1R,2R,3S)-2-(4-fluorophenyl)-3-hydroxycyclopentane-1-carboxylate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium azide 、 草酰氯 、 三氟甲磺酸 、 sodium hydride 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 [(1R,2S,3S)-3-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-2-(4-fluoro-phenyl)-cyclopentyl]-(2-methoxy-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Cyclopentane-based human NK1 antagonists. Part 2: Development of potent, orally active, water-soluble derivatives

  摘要：

  The synthesis and optimization of a cyclopentane-based hNK1 antagonist scaffold 3, having four chiral centers, will be discussed in the context of its enhanced water-solubility properties relative to the marketed anti-emetic hNK1 antagonist EMEND (R) (Aprepitant). Sub-nanomolar hNK1 binding was achieved and oral activity comparable to Aprepitant in two in vivo models will be described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.044