3,4,5-tris(hexyloxy)benzonitrile | 244020-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-tris(hexyloxy)benzonitrile
• 英文别名: Krqltlvwxfjjng-uhfffaoysa-；3,4,5-trihexoxybenzonitrile
• CAS: 244020-36-8
• 化学式: C₂₅H₄₁NO₃
• 分子量: 403.605
• InChiKey: KRQLTLVWXFJJNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(hexyloxy)benzonitrile 在 sodium azide 、 氯化铵 作用下， 以 N-甲基吡咯烷酮 、 乙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Bidirectional Association of Branched Noncovalent Complexes of Tetrazoles and 1,3,5-Tris(4,5-dihydroimidazol-2-yl)benzene in Solution

  摘要：

  Noncovalent 3:1 complexes were obtained by combining acidic tetrazoles with the tribasic 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene (1). A branched structure and the use of solubilizing groups ensured that the resulting complexes dissolved in a range of nonpolar organic solvents. An X-ray crystal structure analysis of a model complex with tetrazole showed a completely planar, C-3-symmetrical, hydrogen-bonded molecule that salt-packed along the crystallographic c axis with an interplanar spacing of 3.31 Angstrom. Model binding studies between a tetrazolate and a protonated 1,3-bis(4,5-dihydroimidazol-2-yl)benzene allowed an association constant of 2470 +/- 400 M-1 to be measured in the competitive solvent mixture CDCl3/CD3OD (97:3). The ionic nature and the extended planarity of the tetrazole complexes' core favored the formation of supramolecular stacks not only in the solid, but also in (nonpolar) solution. Self-association was evidenced by NMR and CD spectroscopy as well as by vapor-pressure osmometry.

  DOI：

  10.1021/jo990830z
• 作为产物：
  描述：

  3,4,5-tris(hexyloxy)benzamide 在 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到3,4,5-tris(hexyloxy)benzonitrile
  参考文献：
  名称：

  Bidirectional Association of Branched Noncovalent Complexes of Tetrazoles and 1,3,5-Tris(4,5-dihydroimidazol-2-yl)benzene in Solution

  摘要：

  Noncovalent 3:1 complexes were obtained by combining acidic tetrazoles with the tribasic 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene (1). A branched structure and the use of solubilizing groups ensured that the resulting complexes dissolved in a range of nonpolar organic solvents. An X-ray crystal structure analysis of a model complex with tetrazole showed a completely planar, C-3-symmetrical, hydrogen-bonded molecule that salt-packed along the crystallographic c axis with an interplanar spacing of 3.31 Angstrom. Model binding studies between a tetrazolate and a protonated 1,3-bis(4,5-dihydroimidazol-2-yl)benzene allowed an association constant of 2470 +/- 400 M-1 to be measured in the competitive solvent mixture CDCl3/CD3OD (97:3). The ionic nature and the extended planarity of the tetrazole complexes' core favored the formation of supramolecular stacks not only in the solid, but also in (nonpolar) solution. Self-association was evidenced by NMR and CD spectroscopy as well as by vapor-pressure osmometry.

  DOI：

  10.1021/jo990830z

文献信息

• Bidirectional Association of Branched Noncovalent Complexes of Tetrazoles and 1,3,5-Tris(4,5-dihydroimidazol-2-yl)benzene in Solution
  作者：Arno Kraft、Frank Osterod、Roland Fröhlich

  DOI：10.1021/jo990830z

  日期：1999.8.1

  Noncovalent 3:1 complexes were obtained by combining acidic tetrazoles with the tribasic 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene (1). A branched structure and the use of solubilizing groups ensured that the resulting complexes dissolved in a range of nonpolar organic solvents. An X-ray crystal structure analysis of a model complex with tetrazole showed a completely planar, C-3-symmetrical, hydrogen-bonded molecule that salt-packed along the crystallographic c axis with an interplanar spacing of 3.31 Angstrom. Model binding studies between a tetrazolate and a protonated 1,3-bis(4,5-dihydroimidazol-2-yl)benzene allowed an association constant of 2470 +/- 400 M-1 to be measured in the competitive solvent mixture CDCl3/CD3OD (97:3). The ionic nature and the extended planarity of the tetrazole complexes' core favored the formation of supramolecular stacks not only in the solid, but also in (nonpolar) solution. Self-association was evidenced by NMR and CD spectroscopy as well as by vapor-pressure osmometry.

表征谱图