(S)-5-(fluoromethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate | 1442433-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (S)-5-(fluoromethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate
• CAS: 1442433-99-9
• 化学式: BF₄*C₁₂H₁₃FN₃
• 分子量: 305.058
• InChiKey: NIHRDJVPQAEAGK-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-5-(fluoromethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 在 四甲基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-(5-(fluoromethyl)-2-phenyl-6,7-dihydro-2H-pyrrolo[2,1-c][1,2,4]triazol-3(5H)-ylid-ene)gold(I) chloride
  参考文献：
  名称：

  The fluorine-NHC gauche effect: a structural and computational study

  摘要：

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.071
• 作为产物：
  描述：

  (S)-5-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]-triazol-2-ium tetrafluoroborate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到(S)-5-(fluoromethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate
  参考文献：
  名称：

  The fluorine-NHC gauche effect: a structural and computational study

  摘要：

  Herein, we report the synthesis and X-ray structural analysis of a collection of fluorinated metal N-heterocyclic carbenes (Ag, Au, Pd, Rh, Ir) and their precursor salts. The common structural feature of these species is a flanking fluoroethyl group, which is either freely rotating or embedded within a bicyclic framework. Solid state analysis confirmed a gauche conformational preference in all cases with the fluorine adopting a syn clinal arrangement (phi([NCCF])similar to 60 degrees) with respect to the triazolium nitrogen at the vicinal position of the NHC. A density functional theory analysis was employed to quantify these effects and evaluate the influence of electronic modulation of the carbenic carbon [(C=N+); neutral carbene (C:); metal-bound carbene (C=M)], on the relative gauche/anti preference, thus highlighting the potential of this conformational phenomenon as a useful molecular design strategy for controlling the topology of organometallic complexes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.071