N-((R)-4-Hydroxy-1-methyl-1-phenyl-butyl)-acetamide | 131154-29-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-((R)-4-Hydroxy-1-methyl-1-phenyl-butyl)-acetamide
• CAS: 131154-29-5
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: VPWBAHOCNXYXCP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-((R)-4-Hydroxy-1-methyl-1-phenyl-butyl)-acetamide 在 氢氧化钾 、 silver nitrate 、 pyridinium chlorochromate 作用下， 生成 (R)-4-Acetylamino-4-phenyl-pentanoic acid
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003
• 作为产物：
  描述：

  苯甲腈 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 双氧水 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 10.5h， 生成 N-((R)-4-Hydroxy-1-methyl-1-phenyl-butyl)-acetamide
  参考文献：
  名称：

  Stereoselective addition reactions of chiral N-benzylidene-p-toluenesulfinamides. Asymmetric syntheses of .beta.- and .gamma.-amino acids

  摘要：

  Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

  DOI：

  10.1021/jo00001a003