(2S)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide | 252049-72-2

• 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: (2S)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide
• 英文别名: (2R)-N-[(2S)-1-(2,6-dimethylphenoxy)propan-2-yl]-2-hydroxy-2-phenylacetamide
• CAS: 252049-72-2
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: HWQHRNSIQKWIAV-DOTOQJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以54.5%的产率得到S-(+)-美西律
  参考文献：
  名称：

  Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)

  摘要：

  Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective antiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmacodynamics during mexiletine therapy. The purpose of this paper is to emphasize the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in the resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite predominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00311-0
• 作为产物：
  描述：

  美西律 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 (2S)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide
  参考文献：
  名称：

  Preparation of highly enantiopure stereoisomers of 1-(2,6-dimethylphenoxy)-2-aminopropane (mexiletine)

  摘要：

  Mexiletine [1-(2,6-dimethylphenoxy)-2-aminopropane], an orally effective antiarrhythmic agent, exhibits enantioselective pharmacokinetics and pharmacodynamics during mexiletine therapy. The purpose of this paper is to emphasize the advantage of tetrahydropyranyl-protected mandelic acid (THPMA) in the resolution of mexiletine enantiomers. Both enantiomers of mexiletine were obtained in 99% enantiomeric excess. Judging by the differential shielding effects in the H-1 and C-13 NMR analyses, we have observed the opposite predominant conformation for the mexiletine mandelates in comparison with the O-methylmandelates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00311-0