(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine | 909784-57-2

• 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: (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine
• 英文别名: trans-3-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylcyclopentanamine；(1S,2R,3R)-3-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-2-phenylcyclopentan-1-amine
• CAS: 909784-57-2
• 化学式: C₂₀H₁₉F₆NO
• 分子量: 403.367
• InChiKey: TZYWVNRQPJYYMS-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine 、 2-碘乙酰胺 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 2-[(1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamino]-acetamide
  参考文献：
  名称：

  Cyclopentane-based human NK1 antagonists. Part 1: Discovery and initial SAR

  摘要：

  An initial investigation of the novel cyclopentane scaffold 6 afforded low nanomolar human NK1 antagonists having enhanced water solubility properties compared to morpholine 1. A synthesis of this cyclopentane scaffold, having three contiguous chiral centers, and the unexpected determination that the 1,2-trans-2,3-trans-ring stereochemistry, as opposed to the cis-ether/phenyl configuration of the known structures 1-5, is optimal for this class of antagonist are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.035
• 作为产物：
  描述：

  1-phenyl-butane-1,2,4-tricarboxylic acid 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium azide 、 草酰氯 、 氢气 、 sodium methylate 、 sodium hydride 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 原甲酸三甲酯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， -10.0~85.0 ℃ 、344.74 kPa 条件下， 反应 80.0h， 生成 (1S,2R,3R)-3-(3,5-Bis-trifluoromethyl-benzyloxy)-2-phenyl-cyclopentylamine
  参考文献：
  名称：

  Cyclopentane-based human NK1 antagonists. Part 1: Discovery and initial SAR

  摘要：

  An initial investigation of the novel cyclopentane scaffold 6 afforded low nanomolar human NK1 antagonists having enhanced water solubility properties compared to morpholine 1. A synthesis of this cyclopentane scaffold, having three contiguous chiral centers, and the unexpected determination that the 1,2-trans-2,3-trans-ring stereochemistry, as opposed to the cis-ether/phenyl configuration of the known structures 1-5, is optimal for this class of antagonist are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.035

文献信息

• Cyclopentane-based human NK1 antagonists. Part 1: Discovery and initial SAR
  作者：Paul E. Finke、Laura C. Meurer、Dorothy A. Levorse、Sander G. Mills、Malcolm MacCoss、Sharon Sadowski、Margaret A. Cascieri、Kwei-Lan Tsao、Gary G. Chicchi、Joseph M. Metzger、D. Euan MacIntyre

  DOI：10.1016/j.bmcl.2006.06.035

  日期：2006.9

  An initial investigation of the novel cyclopentane scaffold 6 afforded low nanomolar human NK1 antagonists having enhanced water solubility properties compared to morpholine 1. A synthesis of this cyclopentane scaffold, having three contiguous chiral centers, and the unexpected determination that the 1,2-trans-2,3-trans-ring stereochemistry, as opposed to the cis-ether/phenyl configuration of the known structures 1-5, is optimal for this class of antagonist are described. (c) 2006 Elsevier Ltd. All rights reserved.