octyl 2,3,4,5,6-pentafluorobenzoate

• 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: octyl 2,3,4,5,6-pentafluorobenzoate
• 英文别名: Octyl pentafluorobenzoate
• 化学式: C₁₅H₁₇F₅O₂
• 分子量: 324.291
• InChiKey: KPGZPQWOOIGSIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4,5,6-pentafluorobenzoate 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 以36%的产率得到octyl 4-azido-2,3,5,6-tetrafluorobenzoate
  参考文献：
  名称：

  Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization

  摘要：

  Triphenylphosphine oxide forms halogen-bonded (XB) complexes with penta-fluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by P-31 NMR spectroscopy in toluene-d, solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self complementary design of these modules facilitates their assembly in both toluene-d(8) and, surprisingly, DCM-d(2) into dimers, with significant stabilities, through the formation of halogen bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in DCM-d(2) solution, through halogen bonding, forming oligomeric assemblies.

  DOI：

  10.1021/acs.joc.6b02822
• 作为产物：
  描述：

  辛醇 、 五氟苯甲酰氯 以 四氢呋喃 为溶剂， 以99%的产率得到octyl 2,3,4,5,6-pentafluorobenzoate
  参考文献：
  名称：

  Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization

  摘要：

  Triphenylphosphine oxide forms halogen-bonded (XB) complexes with penta-fluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by P-31 NMR spectroscopy in toluene-d, solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self complementary design of these modules facilitates their assembly in both toluene-d(8) and, surprisingly, DCM-d(2) into dimers, with significant stabilities, through the formation of halogen bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in DCM-d(2) solution, through halogen bonding, forming oligomeric assemblies.

  DOI：

  10.1021/acs.joc.6b02822

文献信息

• Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization
  作者：Leonardo Maugeri、Tomáš Lébl、David B. Cordes、Alexandra M. Z. Slawin、Douglas Philp

  DOI：10.1021/acs.joc.6b02822

  日期：2017.2.17

  Triphenylphosphine oxide forms halogen-bonded (XB) complexes with penta-fluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by P-31 NMR spectroscopy in toluene-d, solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self complementary design of these modules facilitates their assembly in both toluene-d(8) and, surprisingly, DCM-d(2) into dimers, with significant stabilities, through the formation of halogen bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in DCM-d(2) solution, through halogen bonding, forming oligomeric assemblies.