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

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

  去甲伪麻黄碱 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 50.0h， 生成 (1R,2S)-1-phenyl-2-[(2-pyridylmethyl)amino]propan-1-ol
  参考文献：
  名称：

  Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes

  摘要：

  A series of novel chiral ligands 2a-2f were conveniently prepared from beta -amino alcohols through a two-step reaction and applied to catalyze the enantioselective addition of diethylzinc to benzaldehyde. Among them, ligand 2c was found to show the best asymmetric induction and catalyze the reaction of various aromatic aldehydes to provide (R)-secondary alcohols in up to 98.3% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00336-0

文献信息

• 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.
• Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes
  作者：Yangjie Wu、Hongying Yun、Yusheng Wu、Kuiling Ding、Ying Zhou

  DOI：10.1016/s0957-4166(00)00336-0

  日期：2000.9

  A series of novel chiral ligands 2a-2f were conveniently prepared from beta -amino alcohols through a two-step reaction and applied to catalyze the enantioselective addition of diethylzinc to benzaldehyde. Among them, ligand 2c was found to show the best asymmetric induction and catalyze the reaction of various aromatic aldehydes to provide (R)-secondary alcohols in up to 98.3% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.