(1R,2S)-1-phenyl-2-[(2-pyridylmethyl)amino]-1-propanol

• 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)-1-phenyl-2-[(2-pyridylmethyl)amino]-1-propanol
• 英文别名: (1R,2S)-1-phenyl-2-(pyridin-2-ylmethylamino)propan-1-ol
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: KFRCHOMNEXGBGX-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  去甲麻黄碱 在 sodium triacetoxyborohydride 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 26.0h， 生成 (1R,2S)-1-phenyl-2-[(2-pyridylmethyl)amino]-1-propanol
  参考文献：
  名称：

  用于不对称合成的手性配体：手性N -α-吡啶基甲基氨基醇催化将二乙基锌对映选择性加成到芳族醛中

  摘要：

  由β-氨基醇通过两步顺序方便地制备了一系列手性配体2a – d，并用于催化二乙基锌与苯甲醛的对映选择性加成。其中发现，配体2c对反应显示出最佳的不对称诱导作用，并催化添加到各种芳族醛中以提供高达98.3％ee的（R）-仲醇。

  DOI：

  10.1016/s0040-4039(00)01842-6

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。
• N-Pyridylmethylephedrine derivatives in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines
  作者：Sucharita Banerjee、Jonathan A. Groeper、Jean M. Standard、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2009.08.014

  日期：2009.9

  N-Pyridylmethyl-substituted Ephedra derivatives were synthesized by either direct alkylation or reductive alkylation of (1R,2S)-norephedrine, (1S,2S)-pseudo norephedrine, and (1R,2S)-ephedrine. These derivatives were then employed in asymmetric addition reactions with diethylzinc and aldehydes and diphenylphosphinoylimines. The use of the diastereomers from the Ephedra family allowed for a systematic evaluation of the contribution of the N-pyridylmethyl. (C) 2009 Elsevier Ltd. All rights reserved.
• Chiral ligands for asymmetric synthesis: enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols
  作者：Hongying Yun、Yangjie Wu、Yusheng Wu、Kuiling Ding、Ying Zhou

  DOI：10.1016/s0040-4039(00)01842-6

  日期：2000.12

  A series of chiral ligands 2a–d were conveniently prepared from β-amino alcohols through a two-step sequence and applied to catalysis of enantioselective addition of diethylzinc to benzaldehyde. Among them ligand 2c was found to show the best asymmetric induction for the reaction and catalyze the addition to various aromatic aldehydes to provide (R)-secondary alcohols in up to 98.3% ee.

  由β-氨基醇通过两步顺序方便地制备了一系列手性配体2a – d，并用于催化二乙基锌与苯甲醛的对映选择性加成。其中发现，配体2c对反应显示出最佳的不对称诱导作用，并催化添加到各种芳族醛中以提供高达98.3％ee的（R）-仲醇。