(1S,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxamide

• 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: (1S,2S)-(-)-2-fluoro-2-phenylcyclopropanecarboxamide
• 英文别名: (1S,2S)-2-fluoro-2-phenylcyclopropane-1-carboxamide
• 化学式: C₁₀H₁₀FNO
• 分子量: 179.194
• InChiKey: DYQHKKZKAYZSMO-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  trans-2-fluoro-2-phenylcyclopropanecarboxylic acid chloride 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以30 mg的产率得到(1S,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

文献信息

• COMPLEMENT PATHWAY MODULATORS AND USES THEREOF
  申请人：Altmann Eva

  公开号：US20150141455A1

  公开（公告）日：2015-05-21

  The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物I的公式：（I），本发明的化合物制备方法及其治疗用途。本发明还提供了一种药理活性剂的组合和制药组合物。
• US9815819B2
  申请人：——

  公开号：US9815819B2

  公开（公告）日：2017-11-14
• [EN] COMPLEMENT PATHWAY MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE LA VOIE DU COMPLÉMENT ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2014002051A2

  公开（公告）日：2014-01-03

  The present invention provides a compound of formula I: (I) a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
• New indications for the potential involvement of C–F-bonds in hydrogen bonding
  作者：Roland Fröhlich、Thomas C. Rosen、Oliver G.J. Meyer、Kari Rissanen、Günter Haufe

  DOI：10.1016/j.molstruc.2005.10.033

  日期：2006.4

  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.