(R)-1-benzyl-2-((2,6-dimethylphenoxy)methyl)aziridine

• 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: (R)-1-benzyl-2-((2,6-dimethylphenoxy)methyl)aziridine
• 英文别名: (2R)-1-benzyl-2-[(2,6-dimethylphenoxy)methyl]aziridine
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: DTSZYEFBAKRYCT-DUSLRRAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-benzyl-2-((2,6-dimethylphenoxy)methyl)aziridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 6.0h， 以73%的产率得到L-美西律
  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：

  (2S)-2-[(2,6-dimethylphenoxy)methyl]oxirane 、 苄胺 在 lithium bromide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以64%的产率得到(R)-1-benzyl-2-((2,6-dimethylphenoxy)methyl)aziridine
  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

文献信息

• 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.