4-fluorobicyclo<2.2.2>octane-1-carbaldehyde | 78385-82-7

• 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: 4-fluorobicyclo<2.2.2>octane-1-carbaldehyde
• 英文别名: 4-fluorobicyclo<2.2.2>octane-1-carboxaldehyde；4-fluorobicyclo[2.2.2]octane-1-carbaldehyde
• CAS: 78385-82-7
• 化学式: C₉H₁₃FO
• 分子量: 156.2
• InChiKey: OVSOUYAVBQNARM-UHFFFAOYSA-N

物化性质

• 熔点：
  55-58 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  198.5±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-fluorobicyclo<2.2.2>octane-1-carbaldehyde 在 lead(IV) tetraacetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 29.8h， 生成 N-[(S)-cyano(4-fluorobicyclo[2.2.2]oct-1-yl)methyl]acetamide
  参考文献：
  名称：

  Design and Synthesis of Novel ¹⁹F-Amino Acid: A Promising ¹⁹F NMR Label for Peptide Studies

  摘要：

  Novel aliphatic (19)F-substituted amino acid was designed as a (19)F NMR label for peptide studies. The synthesis was performed in 11 steps and 9% overall yield from a commercially available starting material. The key transformation was a decarboxylative fluorination of an aliphatic carboxylic acid with XeF2 in C6F6.

  DOI：

  10.1021/ol503300m
• 作为产物：
  描述：

  4-(甲氧羰基)双环[2.2.2]辛烷-1-羧酸 在 lithium aluminium tetrahydride 、 二氟代氙 、 三氧化硫吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 4-fluorobicyclo<2.2.2>octane-1-carbaldehyde
  参考文献：
  名称：

  Design and Synthesis of Novel ¹⁹F-Amino Acid: A Promising ¹⁹F NMR Label for Peptide Studies

  摘要：

  Novel aliphatic (19)F-substituted amino acid was designed as a (19)F NMR label for peptide studies. The synthesis was performed in 11 steps and 9% overall yield from a commercially available starting material. The key transformation was a decarboxylative fluorination of an aliphatic carboxylic acid with XeF2 in C6F6.

  DOI：

  10.1021/ol503300m

文献信息

• Polar substituent effects on fluorine-19 chemical shifts of aryl and vinyl fluorides: a fluorine-19 nuclear magnetic resonance study of some 1,1-difluoro-2-(4-substituted-bicyclo[2.2.2]oct-1-yl)ethenes
  作者：William Adcock、Gaik B. Kok

  DOI：10.1021/jo00207a033

  日期：1985.4
• Synthesis of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides
  作者：William Adcock、Anil N. Abeywickrema

  DOI：10.1021/jo00136a028

  日期：1982.7
• ADCOCK, W.;ABEYWICKREMA, A. N., J. ORG. CHEM., 1982, 47, N 15, 2951-2957
  作者：ADCOCK, W.、ABEYWICKREMA, A. N.

  DOI：——

  日期：——
• COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3019196B1

  公开（公告）日：2018-06-06
• Design and Synthesis of Novel ¹⁹F-Amino Acid: A Promising ¹⁹F NMR Label for Peptide Studies
  作者：Dmytro Bandak、Oleg Babii、Roman Vasiuta、Igor V. Komarov、Pavel K. Mykhailiuk

  DOI：10.1021/ol503300m

  日期：2015.1.16

  Novel aliphatic (19)F-substituted amino acid was designed as a (19)F NMR label for peptide studies. The synthesis was performed in 11 steps and 9% overall yield from a commercially available starting material. The key transformation was a decarboxylative fluorination of an aliphatic carboxylic acid with XeF2 in C6F6.