(3S,4R)-1-benzyl-3-fluoro-4-phenyl-3-{4-(trifluoromethyl)phenyl}azetidin-2-one | 1590431-38-1

• 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: (3S,4R)-1-benzyl-3-fluoro-4-phenyl-3-{4-(trifluoromethyl)phenyl}azetidin-2-one
• 英文别名: (3S,4R)-1-benzyl-3-fluoro-4-phenyl-3-[4-(trifluoromethyl)phenyl]azetidin-2-one
• CAS: 1590431-38-1
• 化学式: C₂₃H₁₇F₄NO
• 分子量: 399.388
• InChiKey: JNFMNDJKWBDQQV-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄烯丁胺 在 氯化镍二甲氧基乙烷 、 N-甲基麻黄碱 、 diethylzinc 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3S,4R)-1-benzyl-3-fluoro-4-phenyl-3-{4-(trifluoromethyl)phenyl}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.