1-bromo-3-chloro-5-fluoro-7-iodoadamantane | 479257-17-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-bromo-3-chloro-5-fluoro-7-iodoadamantane
• 英文别名: 1-Bromo-3-iodo-5-fluoro-7-chloroadamantane
• CAS: 479257-17-5
• 化学式: C₁₀H₁₂BrClFI
• 分子量: 393.465
• InChiKey: GDDXCNHXDPVYMD-UHFFFAOYSA-N

物化性质

• 沸点：
  352.7±42.0 °C(Predicted)
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-Bromo-1-chloro-5-fluoro-adamantane 在 全氟己基碘烷 、 铁粉 、 溶剂黄146 作用下， 以65%的产率得到1-bromo-3-chloro-5-fluoro-7-iodoadamantane
  参考文献：
  名称：

  Pseudotetrahedral Polyhaloadamantanes as Chirality Probes:  Synthesis, Separation, and Absolute Configuration

  摘要：

  Pseudotetrahedral, conformationally as well as configurationally stable 1-bromo-3-chloro-5-fluoro- (4) and 1-bromo-3-chloro-5-fluoro-7-iodoadamantane (5) (and some related compounds) were prepared by our recently devised phase-transfer catalytic halogenation protocol; the optical antipodes of 4 were separated by HPLC on chiral phase in ee > 99%, and the absolute configurations were assigned by matching observed and computed circular dichroism spectra. Structure 5 is the first chiral aliphatic hydrocarbon containing all stable (nonradioactive) halogens; its structure was proven by NMR spectroscopy and by X-ray crystal data. We emphasize that the combination of experiment and theory is very powerful in assigning absolute configurations even for molecules without typical chromophors, with small values for the optical rotation, and without an atom at the stereogenic center.

  DOI：

  10.1021/ja0274195