(1R,4R)-5-fluoro-6-phenylbicyclo[2.2.2]oct-5-en-2-one | 1296831-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4R)-5-fluoro-6-phenylbicyclo[2.2.2]oct-5-en-2-one
• CAS: 1296831-77-0
• 化学式: C₁₄H₁₃FO
• 分子量: 216.255
• InChiKey: NQZSYJHNUVXWFU-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(benzo[d]thiazol-2-ylthio)-2-fluoro-1-phenylethan-1-one 在 三乙烯二胺 、 chromium(VI) oxide 、 epi-9-amino quinidine bis(trifluoroacetate) 、 过碘酸 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 (1R,4R)-5-fluoro-6-phenylbicyclo[2.2.2]oct-5-en-2-one
  参考文献：
  名称：

  Asymmetric Organocatalytic Monofluorovinylations

  摘要：

  The development of highly enantio- and c organocatalytic monofluorovinylations is presented. Based on the application of alpha-fluoro beta-keto-benzothiazolesulfones, the formal addition of a monofluorovinylic anion synthon to a range of acydic and cyclic enones, as well as imines, is shown. These procedures give selective access to both E- and Z-isomers of the monofluorovinylated products, which are isolated as the pure diastereoisomers in good to excellent yields with up to 99% ee. Furthermore, the application of this concept for the formation of highly enantioenriched bicylic compounds containing a monofluorovinyl moiety is also described. In addition, a mechanistic rationale for the observed E:Z-selectivities is presented.

  DOI：

  10.1021/ja110624k

文献信息

• Asymmetric Organocatalytic Monofluorovinylations
  作者：Christian Borch Jacobsen、Martin Nielsen、Dennis Worgull、Theo Zweifel、Esben Fisker、Karl Anker Jørgensen

  DOI：10.1021/ja110624k

  日期：2011.5.18

  The development of highly enantio- and c organocatalytic monofluorovinylations is presented. Based on the application of alpha-fluoro beta-keto-benzothiazolesulfones, the formal addition of a monofluorovinylic anion synthon to a range of acydic and cyclic enones, as well as imines, is shown. These procedures give selective access to both E- and Z-isomers of the monofluorovinylated products, which are isolated as the pure diastereoisomers in good to excellent yields with up to 99% ee. Furthermore, the application of this concept for the formation of highly enantioenriched bicylic compounds containing a monofluorovinyl moiety is also described. In addition, a mechanistic rationale for the observed E:Z-selectivities is presented.