(3R,4S)/(3S,4R)-3-fluoro-1,3-dimethyl-4-phenylazetidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)/(3S,4R)-3-fluoro-1,3-dimethyl-4-phenylazetidin-2-one
• 英文别名: (3R,4S)-3-fluoro-1,3-dimethyl-4-phenylazetidin-2-one
• 化学式: C₁₁H₁₂FNO
• 分子量: 193.221
• InChiKey: MRNBOACCOBVUAZ-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯亚甲基甲胺 在 正丁基锂 、 diethylzinc 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.17h， 生成 (3R,4S)/(3S,4R)-3-fluoro-1,3-dimethyl-4-phenylazetidin-2-one
  参考文献：
  名称：

  Direct and Diastereoselective Alkylation and Aldol Reactions of α-Bromo-α-fluoro-β-lactams

  摘要：

  Herein, we describe the development of a method for the direct alkylation and aldol reaction of alpha-bromo-alpha-fluoro-beta-lactams. This method provides facile access to a wide range of 3-alkyl- and 3-hydroxyalkyl-fluoro-beta-lactams in good yields under mild conditions. The products were obtained with complete diastereoselectivity with regard to the relative configuration of the beta-lactam ring at C3 and C4 positions. The reaction conditions were tolerant of a broad range of electrophiles, which highlights the overall scope and utility of this procedure.

  DOI：

  10.1021/jo401072h

文献信息

• Direct and Diastereoselective Alkylation and Aldol Reactions of α-Bromo-α-fluoro-β-lactams
  作者：Atsushi Tarui、Naoto Kawashima、Tetsuya Kawakita、Kazuyuki Sato、Masaaki Omote、Akira Ando

  DOI：10.1021/jo401072h

  日期：2013.8.16

  Herein, we describe the development of a method for the direct alkylation and aldol reaction of alpha-bromo-alpha-fluoro-beta-lactams. This method provides facile access to a wide range of 3-alkyl- and 3-hydroxyalkyl-fluoro-beta-lactams in good yields under mild conditions. The products were obtained with complete diastereoselectivity with regard to the relative configuration of the beta-lactam ring at C3 and C4 positions. The reaction conditions were tolerant of a broad range of electrophiles, which highlights the overall scope and utility of this procedure.