(3S,4R)-1-benzyl-3-bromo-3-fluoro-4-(4-methoxycarbonylphenyl)azetidin-2-one | 1590431-26-7

• 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: (3S,4R)-1-benzyl-3-bromo-3-fluoro-4-(4-methoxycarbonylphenyl)azetidin-2-one
• 英文别名: methyl 4-[(2R,3S)-1-benzyl-3-bromo-3-fluoro-4-oxoazetidin-2-yl]benzoate
• CAS: 1590431-26-7
• 化学式: C₁₈H₁₅BrFNO₃
• 分子量: 392.224
• InChiKey: WGAZANPRCALFDI-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二溴氟乙酸乙酯 、 4-carbomethoxybenzylidenebenzylamine 在 diethylzinc 、 (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(3S,4R)-1-benzyl-3-bromo-3-fluoro-4-(4-methoxycarbonylphenyl)azetidin-2-one
  参考文献：
  名称：

  Ligand-Promoted Asymmetric Imino-Reformatsky Reaction of Ethyl Dibromofluoroacetate

  摘要：

  An enantioselective Reformatsky reaction has been developed for the reaction of ethyl dibromofluoroacetate (1) with an imine. This method represents the first ligand-promoted imino-Reformatslcy approach to use a halofluoroacetate. The use of an amino alcohol ligand allowed for the preparation of enantioenriched alpha-bromo-alpha-fluoro-beta-lactams in good yields with enantioselectivities up to 96% ee. This process also provided access to beta-lactam rings bearing two stereogenic centers.

  DOI：

  10.1021/ol500631j

文献信息

• Ligand-Promoted Asymmetric Imino-Reformatsky Reaction of Ethyl Dibromofluoroacetate
  作者：Atsushi Tarui、Haruka Nishimura、Takeshi Ikebata、Asuka Tahira、Kazuyuki Sato、Masaaki Omote、Hideki Minami、Yoshihisa Miwa、Akira Ando

  DOI：10.1021/ol500631j

  日期：2014.4.18

  An enantioselective Reformatsky reaction has been developed for the reaction of ethyl dibromofluoroacetate (1) with an imine. This method represents the first ligand-promoted imino-Reformatslcy approach to use a halofluoroacetate. The use of an amino alcohol ligand allowed for the preparation of enantioenriched alpha-bromo-alpha-fluoro-beta-lactams in good yields with enantioselectivities up to 96% ee. This process also provided access to beta-lactam rings bearing two stereogenic centers.