2-[benzyl-[(2R)-1-phenoxypropan-2-yl]amino]ethanol | 34238-86-3

• 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: 2-[benzyl-[(2R)-1-phenoxypropan-2-yl]amino]ethanol
• CAS: 34238-86-3
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: LYNJRXJVOBYDCM-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[benzyl-[(2R)-1-phenoxypropan-2-yl]amino]ethanol 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 8.0h， 以56%的产率得到phenoxybenzamine
  参考文献：
  名称：

  Chiral aziridine ring opening: facile synthesis of (R)-mexiletine and (R)-phenoxybenzamine hydrochloride

  摘要：

  A simple and efficient synthesis of chiral drugs (R)-mexiletine 1, an anti-arrhythmic drug and (R)-phenoxybenzamine hydrochloride 2, an anti-hypertensive drug has been described via controlled reductive ring opening of chiral aziridine as a key step. The target compounds 1 and 2 were obtained in overall yields of 34% and 10.5%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.032
• 作为产物：
  描述：

  苯基缩水甘油醚 在 lithium aluminium tetrahydride 、 (S,S)-(salen)cobalt(III)(OAc) 、 potassium carbonate 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 107.25h， 生成 2-[benzyl-[(2R)-1-phenoxypropan-2-yl]amino]ethanol
  参考文献：
  名称：

  A facile enantioselective synthesis of enantiomerically pure (R)-phenoxybenzamine hydrochloride using the hydrolytic kinetic resolution method

  摘要：

  A practical and highly efficient enantioselective synthesis of (R)-phenoxybenzamine hydrochloride has been described for the first time using Jacobsen's hydrolytic kinetic resolution of a terminal epoxide as a key step and source of chirality. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.011

文献信息

• Tetrahedron Lett. 2015, 56, 5269-5271
  作者：

  DOI：——

  日期：——
• Chiral aziridine ring opening: facile synthesis of (R)-mexiletine and (R)-phenoxybenzamine hydrochloride
  作者：N. Viswanadh、R. Velayudham、S. Jambu、M. Sasikumar、M. Muthukrishnan

  DOI：10.1016/j.tetlet.2015.07.032

  日期：2015.9

  A simple and efficient synthesis of chiral drugs (R)-mexiletine 1, an anti-arrhythmic drug and (R)-phenoxybenzamine hydrochloride 2, an anti-hypertensive drug has been described via controlled reductive ring opening of chiral aziridine as a key step. The target compounds 1 and 2 were obtained in overall yields of 34% and 10.5%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
• A facile enantioselective synthesis of enantiomerically pure (R)-phenoxybenzamine hydrochloride using the hydrolytic kinetic resolution method
  作者：Milind D. Nikalje、Murugesan Sasikumar、Murugan Muthukrishnan

  DOI：10.1016/j.tetasy.2010.11.011

  日期：2010.12

  A practical and highly efficient enantioselective synthesis of (R)-phenoxybenzamine hydrochloride has been described for the first time using Jacobsen's hydrolytic kinetic resolution of a terminal epoxide as a key step and source of chirality. (C) 2010 Elsevier Ltd. All rights reserved.