(R,E)-3-(1-fluoro-2-(naphthalen-2-yl)vinyl)cyclohexanone | 1296831-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R,E)-3-(1-fluoro-2-(naphthalen-2-yl)vinyl)cyclohexanone
• 英文别名: (3R)-3-[(E)-1-fluoro-2-naphthalen-2-ylethenyl]cyclohexan-1-one
• CAS: 1296831-50-9
• 化学式: C₁₈H₁₇FO
• 分子量: 268.331
• InChiKey: HZWSZQNOPMHPGF-YCPFAOKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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-ylsulfonyl)-2-fluoro-1-(naphthalen-2-yl)ethanone 在 锂硼氢 、 epi-9-amino quinidine bis(trifluoroacetate) 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (R,E)-3-(1-fluoro-2-(naphthalen-2-yl)vinyl)cyclohexanone
  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.