(R)-N-methyl-3-(o-methoxyphenyl)-4-phenylbutanamide | 178382-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-N-methyl-3-(o-methoxyphenyl)-4-phenylbutanamide
• 英文别名: (3R)-3-(2-methoxyphenyl)-N-methyl-4-phenylbutanamide
• CAS: 178382-61-1
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: OYFKPJQBMWSMDQ-OAHLLOKOSA-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-methyl-3-(o-methoxyphenyl)-4-phenylbutanamide 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (R)-4-Benzyl-chroman-2-one
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r
• 作为产物：
  描述：

  溴甲苯 、 N-methyl-3-(o-methoxyphenyl)propanamide 在 甲基叔丁基醚 、 仲丁基锂 、 鹰爪豆碱 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到(R)-N-methyl-3-(o-methoxyphenyl)-4-phenylbutanamide
  参考文献：
  名称：

  Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides:  Diastereoselective and Enantioselective Substitutions

  摘要：

  The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity, Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.

  DOI：

  10.1021/jo952223r