(3S,4R)-1-benzyl-3-fluoro-3,4-diphenylazetidin-2-one | 1590431-36-9

• 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-3,4-diphenylazetidin-2-one
• CAS: 1590431-36-9
• 化学式: C₂₂H₁₈FNO
• 分子量: 331.389
• InChiKey: APMDSUHXPDHMBH-IRLDBZIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  苯基溴化镁 在 NiBr2*diglyme 、 异丁醇 、 4,4'-二叔丁基-2,2'-二吡啶 、 lithium tert-butoxide 作用下， 以 正己烷 、 苯 为溶剂， 反应 1.33h， 生成 (3S,4R)-1-benzyl-3-fluoro-3,4-diphenylazetidin-2-one
  参考文献：
  名称：

  Stereoselective Suzuki Coupling Reaction of an α-Bromo-α-fluoro-β-lactam

  摘要：

  A new strategy has been developed for the synthesis of alpha-aryl-alpha-fluoro-beta-lactams via the Suzuki cross-coupling of alpha-bromo-alpha-fluoro-beta-lactam with a range of different aryl-(9-BBN) reagents. This method provides facile access to multisubstituted alpha-fluoro-beta-lactams in a diastereoselective manner. The synthetic utility of alpha-bromo-alpha-fluoro-beta-lactam has been demonstrated by the arylation of alpha-bromo-alpha-fluoro-beta-lactam.

  DOI：

  10.1055/s-0034-1379637

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.