(1R,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxylic acid | 888725-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxylic acid
• 英文别名: (1S,2S)-2-fluoro-2-phenylcyclopropanecarboxylic acid；rel-(1R,2S)-2-fluoro-2-phenylcyclopropane-1-carboxylic acid；(1R,2S)-2-fluoro-2-phenylcyclopropane-1-carboxylic acid
• CAS: 888725-97-1
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: ULOVTWLQHAOUKT-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxylic acid 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 6.5h， 生成 (1R,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxamide
  参考文献：
  名称：

  New indications for the potential involvement of C–F-bonds in hydrogen bonding

  摘要：

  Solid state structures of a selection of 2-fluoro-2-phenylcyclopropane derivatives were examined by X-ray crystallography in order to identify short intermolecular contacts of C-F groups to H-X moieties (X = C, N). Particularly, several cis-configured fluorinated phenylcyclopropane derivatives showed extremely close intermolecular contacts. The shortest of such C-(HF)-F-...-C-distances (2.17 angstrom, C-F-H angle 162 degrees) was found in (IS,2R)-(2-fluoro-2-phenylcyclopropyl)methyl N-(4-bromophenyl)carbamate (8) and the closest N-(HF)-F-...-C-interaction (2.01 angstrom, C-F-H angle 167 degrees) was found in (+/-)-cis-2-fluoro-2-phenylcyclopropyl carboxamide (4). Comparison of the structures of several of the fluorinated cyclopropares with those of the non-fluorinated counterparts revealed that close intermolecular contacts of fluorine substituents to hydrogen atoms are not solely due to crystal packing effects, but are also caused by weak X-H... F-C hydrogen bridges. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.10.033
• 作为产物：
  描述：

  (1R,2S)-(-)-(2-fluoro-2-phenylcyclopropyl)methanol 在 potassium permanganate 、 四丁基溴化铵 作用下， 以 水 、 苯 为溶剂， 反应 17.0h， 生成 (1R,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxylic acid
  参考文献：
  名称：

  New indications for the potential involvement of C–F-bonds in hydrogen bonding

  摘要：

  Solid state structures of a selection of 2-fluoro-2-phenylcyclopropane derivatives were examined by X-ray crystallography in order to identify short intermolecular contacts of C-F groups to H-X moieties (X = C, N). Particularly, several cis-configured fluorinated phenylcyclopropane derivatives showed extremely close intermolecular contacts. The shortest of such C-(HF)-F-...-C-distances (2.17 angstrom, C-F-H angle 162 degrees) was found in (IS,2R)-(2-fluoro-2-phenylcyclopropyl)methyl N-(4-bromophenyl)carbamate (8) and the closest N-(HF)-F-...-C-interaction (2.01 angstrom, C-F-H angle 167 degrees) was found in (+/-)-cis-2-fluoro-2-phenylcyclopropyl carboxamide (4). Comparison of the structures of several of the fluorinated cyclopropares with those of the non-fluorinated counterparts revealed that close intermolecular contacts of fluorine substituents to hydrogen atoms are not solely due to crystal packing effects, but are also caused by weak X-H... F-C hydrogen bridges. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.10.033