(2,4,6-tris(4-etynylbenzonitrile)phenoxy)ethanol | 246247-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2,4,6-tris(4-etynylbenzonitrile)phenoxy)ethanol
• 英文别名: (2,4,6-tris(4-ethynylbenzonitrile)phenoxy)ethanol；4-[2-[3,5-Bis[2-(4-cyanophenyl)ethynyl]-4-(2-hydroxyethoxy)phenyl]ethynyl]benzonitrile
• CAS: 246247-29-0
• 化学式: C₃₅H₁₉N₃O₂
• 分子量: 513.555
• InChiKey: LKXOAHUZSXCPES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 (2,4,6-tris(4-etynylbenzonitrile)phenoxy)ethanol 在 2,6-二叔丁基吡啶 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 tert-butyl((2,4,6-tris((4-cyanophenyl)ethynyl)phenoxy)ethoxy)dimethylsilane
  参考文献：
  名称：

  Porous Siloxane Linked Phenylacetylene Nitrile Silver Salts from Solid State Dimerization and Low Polymerization

  摘要：

  Three 3-fold symmetric rigid backbone phenylacetylene nitrile molecules have been prepared to which one to six hydroxy side chains have been attached. These molecules were cocrystallized with silver(I) trifluoromethanesulfonate (triflate) to form microcrystalline porous solids. X-ray powder data show that all three crystal structures are isotypic to the crystal structures found in previous single crystal studies on related systems. Structural models based on these earlier single crystal structures have theoretical powder patterns in reasonable agreement with the experimentally observed patterns. These crystalline materials were allowed to react with silyl triflates. H-1 NMR and X-ray powder studies show that the silyl triflate groups react with the alcohol terminated side chains to form siloxane linkages with retention of the initial crystal structure. In the case of 1,3,5-tris(4-((4-cyanophenyl)ethynyl)-2-((4-hydroxybutoxy)methyl)phenylethynyl)benzene, a phenylacetylene nitrile molecule with three alcohol side chains, the introduction of di-tert-butylsilyl bis(trifluoromethanesulfonate) resulted in the formation of low polymers with average weight molecular weight of 7 x 10(4). This polymerized material shows increased chemical robustness in contrast to the unpolymerized material. It is stable in a variety of solvents, including overnight exposure to boiling water. Exchange experiments with toluene show that this final material is still porous.

  DOI：

  10.1021/ja0009119
• 作为产物：
  描述：

  (2,4,6-tris(trimethylsilylethynyl)phenoxy)ethanol 在 bis(triphenylphosphine)palladium(II)-chloride copper(l) iodide 、 四丁基氟化铵 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.08h， 生成 (2,4,6-tris(4-etynylbenzonitrile)phenoxy)ethanol
  参考文献：
  名称：

  Variable Pore Size, Variable Chemical Functionality, and an Example of Reactivity within Porous Phenylacetylene Silver Salts

  摘要：

  Investigations on molecular variants of the 3-fold symmetric 1,3,5-tris(4-ethynylbenzonitrile)benzene crystallized with silver triflate revealed a nearly invariant pseudohexagonal porous structure type. Modifications involved the attachment of pendant groups to the central aromatic ring of the parent molecule. Pendant groups include the vinyl group, stilbene, the chiral group myrtanol, and groups with different chemical functionalities such as alcohols, ethers, and esters. Modifications also included the addition of elongated spacer units between the central benzene ring and the peripheral nitrile groups. In these molecules the acetylene bridges of 1,3,5-tris(4-ethynylbenzonitrile)benzene were replaced with diacetylene, ethynylbenzene, and diethynylbenzene type units. Single-crystal refinements for pentoxy-2,4,6-tris(4-ethynylbenzonitril)benzene.AgOTf and 1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf as well as powder data on 12 crystalline phases showed the consistent formation of pseudohexagonal channels, demonstrating that the parent porous architecture is stable both to functional modification of the interior of the channel as well as to enlargement of the pores. Pentoxy-2,4,6-tris(4-ethynylbenzonitrile)benzene.AgOTf refined in the monoclinic space group Am. 1,3,5-Tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf was found to be triclinic with space group P (1) over bar. These crystals have pseudohexagonal channels respectively 15 and 25 Angstrom in diameter. Cell constants based on powder data are compatible with channel diameters ranging from 10 to 30 Angstrom. The latter channel diameters are among the largest known for organic porous solids. The introduction of the chiral myrtanol unit led to the preparation of a chiral porous solid. The thermal and chemical stabilities of these phases were investigated. The pseudohexagonal structure proved stable to complete solvent loss from the channel. It was found in the case of a host with alcohol functionality that an acid anhydride guest, trifluoroacetic anhydride, reacted with the host to form an ester with retention of the porous structure type.

  DOI：

  10.1021/ja991100b