(2S)-N-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide

• 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-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide
• 英文别名: (2S)-N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethyl-3-phenylpropanamide
• 化学式: C₂₀H₂₅NO₂
• 分子量: 311.424
• InChiKey: YBSOZNKAYZZSLZ-BXWFABGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  麻黄碱 、 2-methyl-3-phenylpropionic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 生成 (2S)-N-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethyl-3-phenylpropionamide
  参考文献：
  名称：

  A Convenient, NMR-Based Method for the Analysis of Diastereomeric Mixtures of Pseudoephedrine Amides

  摘要：

  Amides of pseudoephedrine and ephedrine are shown to undergo highly stereospecific, invertive cyclization to form 4,5-dihydro-3,4-dimethyl-5-phenyl-1,3-oxazolium triflate derivatives in the presence of triflic anhydride-pyridine. H-1 NMR spectra of the unpurified reaction products are remarkably clean, with sharp, well-defined peaks, and allow for rapid assessment of the diastereomeric purities of the starting amides.

  DOI：

  10.1021/ol0628762

文献信息

• A Convenient, NMR-Based Method for the Analysis of Diastereomeric Mixtures of Pseudoephedrine Amides
  作者：William J. Chain、Andrew G. Myers

  DOI：10.1021/ol0628762

  日期：2007.1.1

  Amides of pseudoephedrine and ephedrine are shown to undergo highly stereospecific, invertive cyclization to form 4,5-dihydro-3,4-dimethyl-5-phenyl-1,3-oxazolium triflate derivatives in the presence of triflic anhydride-pyridine. H-1 NMR spectra of the unpurified reaction products are remarkably clean, with sharp, well-defined peaks, and allow for rapid assessment of the diastereomeric purities of the starting amides.