(1R,4S,4aS,5R,8S,12R,13R)-12-bromo-13-fluorooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-9,11-dione | 1464812-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,4S,4aS,5R,8S,12R,13R)-12-bromo-13-fluorooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-9,11-dione
• CAS: 1464812-70-1
• 化学式: C₁₄H₁₄BrFO₃
• 分子量: 329.166
• InChiKey: IMEDZFCVTPHSJB-GROFJEMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1R,4S,4aR,5R,8S,12S,13S)-13-fluoro-9,11-dioxooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalen-12-yl trifluoromethanesulfonate 在 potassium bromide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以26%的产率得到(1R,4S,4aS,5R,8S,12R,13R)-12-bromo-13-fluorooctahydro-1,4:5,8-dimethano-4a,8a-(methanooxymethano)naphthalene-9,11-dione
  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