(2R,3S)-1-(3-(trifluoromethyl)benzylamino)-3-(dibenzylamino)-5-methylhexan-2-ol | 1383132-22-6

• 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: (2R,3S)-1-(3-(trifluoromethyl)benzylamino)-3-(dibenzylamino)-5-methylhexan-2-ol
• 英文别名: (2R,3S)-3-(dibenzylamino)-5-methyl-1-[[3-(trifluoromethyl)phenyl]methylamino]hexan-2-ol
• CAS: 1383132-22-6
• 化学式: C₂₉H₃₅F₃N₂O
• 分子量: 484.605
• InChiKey: IWFNHFLLOBYYBH-WUFINQPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(三氟甲基)苯甲胺 、 以 乙醇 为溶剂， 反应 20.0h， 生成 (2R,3S)-1-(3-(trifluoromethyl)benzylamino)-3-(dibenzylamino)-5-methylhexan-2-ol 、 (2S,3S)-1-(3-(trifluoromethyl)benzylamino)-3-(dibenzylamino)-5-methylhexan-2-ol
  参考文献：
  名称：

  Diastereoselective Synthesis ofN,N-Dibenzyl-Protected Aminoalkyl Hydroxyethylamines: Key Building Blocks for Hydroxyethylamine-Based BACE1 Inhibitor

  摘要：

  L-Amino acids were reduced with NaBH4 followed by reacting with benzyl bromide to give N,N-dibenzyl-protected aminoalkyl ethanol 3, which in turn underwent a Swern oxidation, a Johnson-Corey-Chaykovsky reaction, and a nucleophilic reaction to afford N, N-dibenzyl-protected aminoalkyl hydroxyethylamine 6 with a diastereomer ratio 2.5 similar to 2.9:1 of (2R, 3S)-6:(2S, 3S)-6.

  DOI：

  10.1080/00397911.2011.572217

文献信息

• Diastereoselective Synthesis of<i>N,N</i>-Dibenzyl-Protected Aminoalkyl Hydroxyethylamines: Key Building Blocks for Hydroxyethylamine-Based BACE1 Inhibitor
  作者：Jie Wu、Shanyun Gao、Guochao Liao、Hansen Lin、Aihua Nie

  DOI：10.1080/00397911.2011.572217

  日期：2012.10

  L-Amino acids were reduced with NaBH4 followed by reacting with benzyl bromide to give N,N-dibenzyl-protected aminoalkyl ethanol 3, which in turn underwent a Swern oxidation, a Johnson-Corey-Chaykovsky reaction, and a nucleophilic reaction to afford N, N-dibenzyl-protected aminoalkyl hydroxyethylamine 6 with a diastereomer ratio 2.5 similar to 2.9:1 of (2R, 3S)-6:(2S, 3S)-6.