3-((S)-1-((S)-1-phenylethylamino)ethyl)phenol | 1017234-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-((S)-1-((S)-1-phenylethylamino)ethyl)phenol
• 英文别名: 3-[(1S)-1-[[(1S)-1-phenylethyl]amino]ethyl]phenol
• CAS: 1017234-21-7
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: BQFQIRIOPXMTEQ-STQMWFEESA-N

物化性质

• 沸点：
  373.5±22.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((S)-1-((S)-1-phenylethylamino)ethyl)phenol 在 甲酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0~70.0 ℃ 、517.12 kPa 条件下， 反应 29.0h， 生成 3-(1-(S)-(N,N-二甲基氨基)乙基)苯酚
  参考文献：
  名称：

  General Strategy for Large-Scale Synthesis of (+)-Rivastigmine and (+)-NPS R-568

  摘要：

  An economically viable strategy for the total synthesis of (+)-rivastigmine and (+)-NPS R-568 has been reported. The strategy involves regioselective hydrogenation of diastereomerically pure bis amine to realize the desired alpha-methyl chiral substituted benzyl amine. The route is economical, scalable, and versatile enough to be adapted to similar classes of compounds.

  DOI：

  10.1080/00397911.2010.527425
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 3-((S)-1-((S)-1-phenylethylamino)ethyl)phenol
  参考文献：
  名称：

  General Strategy for Large-Scale Synthesis of (+)-Rivastigmine and (+)-NPS R-568

  摘要：

  An economically viable strategy for the total synthesis of (+)-rivastigmine and (+)-NPS R-568 has been reported. The strategy involves regioselective hydrogenation of diastereomerically pure bis amine to realize the desired alpha-methyl chiral substituted benzyl amine. The route is economical, scalable, and versatile enough to be adapted to similar classes of compounds.

  DOI：

  10.1080/00397911.2010.527425

文献信息

• Stereoselective Metal-Free Reduction of Chiral Imines in Batch and Flow Mode: A Convenient Strategy for the Synthesis of Chiral Active Pharmaceutical Ingredients
  作者：Davide Brenna、Maurizio Benaglia、Riccardo Porta、Silvia Fernandes、Anthony J. Burke

  DOI：10.1002/ejoc.201601268

  日期：2017.1.3

  The convenient, metal-free reduction of imines that contain an inexpensive and removable chiral auxiliary allowed for the synthesis of the immediate precursors of chiral active pharmaceutical ingredients (APIs). This protocol was carried out under batch and flow conditions to give the correspoding products in high yields with almost complete stereocontrol. In the presence of trichlorosilane, an inexpensive

  包含廉价且可移除的手性助剂的亚胺的方便、无金属还原允许合成手性活性药物成分 (API) 的直接前体。该协议是在批量和流动条件下进行的，以提供几乎完全立体控制的高产率的相应产品。在三氯硅烷、一种廉价且无毒的还原剂和非手性路易斯碱（如 N,N-二甲基甲酰胺）的存在下，成功地完成了利凡斯明、拟钙剂 NPS R-568 和 Rho 激酶抑制剂的正式合成。首次在连续流动条件下在微反应器或介观反应器中有效地进行非对映选择性亚胺还原和辅助去除，
• General Strategy for Large-Scale Synthesis of (+)-Rivastigmine and (+)-NPS R-568
  作者：Ramakrishna Rao、Mukesh Padmakar Shewalkar、Ramadevi Nandipati、Jhillu Singh Yadav、Mukkanti Khagga、Devanand Baburao Shinde

  DOI：10.1080/00397911.2010.527425

  日期：2012.2.15

  An economically viable strategy for the total synthesis of (+)-rivastigmine and (+)-NPS R-568 has been reported. The strategy involves regioselective hydrogenation of diastereomerically pure bis amine to realize the desired alpha-methyl chiral substituted benzyl amine. The route is economical, scalable, and versatile enough to be adapted to similar classes of compounds.