1-fluoro-3-chloro-adamantane | 60389-52-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1-fluoro-3-chloro-adamantane
• 英文别名: 1-Chloro-3-fluoradamantan；1-Fluor-3-chloradamantan；1-Chloro-3-fluoroadamantane
• CAS: 60389-52-8
• 化学式: C₁₀H₁₄ClF
• 分子量: 188.673
• InChiKey: AVLYRMVIYOSHAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 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

• 作为反应物：
  描述：

  1-fluoro-3-chloro-adamantane 在 四溴化碳 、 四丁基溴化铵 作用下， 以 氟苯 为溶剂， 以21%的产率得到3-Bromo-1-chloro-5-fluoro-adamantane
  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
• 作为产物：
  描述：

  1-氟金刚烷 在 四氯化碳 作用下， 生成 1-fluoro-3-chloro-adamantane
  参考文献：
  名称：

  Perkins,R.R.; Pincock,R.E., Canadian Journal of Chemistry, 1978, vol. 56, p. 1269 - 1272

  摘要：

  DOI：

文献信息

• Perkins,R.R.; Pincock,R.E., Canadian Journal of Chemistry, 1978, vol. 56, p. 1269 - 1272
  作者：Perkins,R.R.、Pincock,R.E.

  DOI：——

  日期：——
• Pseudotetrahedral Polyhaloadamantanes as Chirality Probes:  Synthesis, Separation, and Absolute Configuration
  作者：Peter R. Schreiner、Andrey A. Fokin、Oliver Lauenstein、Yoshio Okamoto、Tsuneki Wakita、Christopher Rinderspacher、Gregory H. Robinson、Jason K. Vohs、Charles F. Campana

  DOI：10.1021/ja0274195

  日期：2002.11.1

  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.