cis-4-(chlorophenyl)-3-methoxy-1-α-naphthyl-2-azetidinone | 135569-51-6

• 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: cis-4-(chlorophenyl)-3-methoxy-1-α-naphthyl-2-azetidinone
• 英文别名: (3S,4R)-4-(4-chlorophenyl)-3-methoxy-1-naphthalen-1-ylazetidin-2-one
• CAS: 135569-51-6
• 化学式: C₂₀H₁₆ClNO₂
• 分子量: 337.806
• InChiKey: CKHYKVHNHWVMGJ-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 生成 cis-4-(chlorophenyl)-3-methoxy-1-α-naphthyl-2-azetidinone
  参考文献：
  名称：

  Cycloaddition of (N-alkyl-N-phenylamino)ketene with imines

  摘要：

  (N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a [2 + 2] cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones. The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition. The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines. In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine. These results are discussed in terms of a two-step zwitterionic intermediate.

  DOI：

  10.1021/jo00021a029