(1R,4S,4aR,5S,8R,12R,13R)-13-fluoro-9,11-dioxooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-12-carbonitrile | 1464812-74-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4S,4aR,5S,8R,12R,13R)-13-fluoro-9,11-dioxooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-12-carbonitrile
• CAS: 1464812-74-5
• 化学式: C₁₅H₁₄FNO₃
• 分子量: 275.279
• InChiKey: HDPQQYKDFZYUFA-NVFQDSKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  sodium cyanide 、 (1R,4S,4aR,5R,8S,12S,13S)-13-fluoro-9,11-dioxooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalen-12-yl trifluoromethanesulfonate 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以79%的产率得到(1R,4S,4aR,5S,8R,12R,13R)-13-fluoro-9,11-dioxooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-12-carbonitrile
  参考文献：
  名称：

  Modulating “Jousting” C–F---H–C Interactions with a Bit of Hydrogen Bonding

  摘要：

  We have synthesized a series of molecules wherein very close C-F-H-C sigma-bond interactions, which we have termed "jousting", can be perturbed through both red- and blue-shifted hydrogen bonding effects. These interactions were induced by the placement of various functional groups geminal to the H-C bond. "Jousting" interactions appear to be an admixture of F-H hydrogen bonding and C-H bond compression. The associated electronic effects from changes in the functional group at the X-position were also studied.

  DOI：

  10.1021/jo4018205