(1R,2S)-2-((naphthalen-1-ylmethyl)amino)-1-phenylpropan-1-ol | 1010389-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-2-((naphthalen-1-ylmethyl)amino)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-2-(naphthalen-1-ylmethylamino)-1-phenylpropan-1-ol
• CAS: 1010389-61-3
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: HMOBWRBTOISBJV-YWZLYKJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 (1R,2S)-2-((naphthalen-1-ylmethyl)amino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  β-Amino alcohols derived from (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes

  摘要：

  A family of N-alkylnorephedrine and N-alkylpseudonorephedrine derived ligands were prepared and applied in the asymmetric alkylation of benzaldehyde using diethylzinc. The absolute configuration of the addition product was directed primarily by the benzylic position of the Ephedra alkaloid, while the magnitude of the enantiomeric ratio was heavily influenced by the nitrogen substituent. However, sterically demanding substituents at the nitrogen position caused the enantioselectivity to be the same for the two diastereomeric systems. Among the ligands that were prepared, it was determined that the N-cyclooctylpseudonorephedrine derivative 7b yielded the highest enantiomeric ratios (87.5:12.5 to 91.0:9.0) when applied in the catalytic asymmetric addition of diethylzinc to aldehydes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.027

文献信息

• Design of a Genetic Algorithm for the Simulated Evolution of a Library of Asymmetric Transfer Hydrogenation Catalysts
  作者：Nicolas Vriamont、Bernadette Govaerts、Pierre Grenouillet、Claude de Bellefon、Olivier Riant

  DOI：10.1002/chem.200802192

  日期：2009.6.15

  Breeding new catalysts: A library of 1980 catalysts was designed for asymmetric hydrogen transfer to acetophenone. The library was submitted to evaluation and further simulated evolution experiments, based on a genetic algorithm (see scheme). We demonstrated that it was easily possible to get 5–6 of the ten best catalysts, while investigating only 10% of the library.

  培育新的催化剂：设计了1980个催化剂库，用于将氢不对称地转移到苯乙酮中。基于遗传算法（请参阅方案），该库已提交评估和进一步的模拟进化实验。我们证明，很容易就能获得十种最佳催化剂中的5–6种，而仅需研究10％的催化剂。
• β-Amino alcohols derived from (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes
  作者：Raleigh W. Parrott、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2007.11.027

  日期：2008.1

  A family of N-alkylnorephedrine and N-alkylpseudonorephedrine derived ligands were prepared and applied in the asymmetric alkylation of benzaldehyde using diethylzinc. The absolute configuration of the addition product was directed primarily by the benzylic position of the Ephedra alkaloid, while the magnitude of the enantiomeric ratio was heavily influenced by the nitrogen substituent. However, sterically demanding substituents at the nitrogen position caused the enantioselectivity to be the same for the two diastereomeric systems. Among the ligands that were prepared, it was determined that the N-cyclooctylpseudonorephedrine derivative 7b yielded the highest enantiomeric ratios (87.5:12.5 to 91.0:9.0) when applied in the catalytic asymmetric addition of diethylzinc to aldehydes. (c) 2007 Elsevier Ltd. All rights reserved.