bis(2,4-dihydroxy-5-hexyl-1-phenyl)(2-pyridyl)methane | 137300-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: bis(2,4-dihydroxy-5-hexyl-1-phenyl)(2-pyridyl)methane
• 英文别名: 4-Hexyl-6-[(5-hexyl-2,4-dihydroxyphenyl)-pyridin-2-ylmethyl]benzene-1,3-diol
• CAS: 137300-41-5
• 化学式: C₃₀H₃₉NO₄
• 分子量: 477.644
• InChiKey: SOTBKFKMVQSJBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  93.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 bis(2,4-dihydroxy-5-hexyl-1-phenyl)(2-pyridyl)methane 在 吡啶 作用下， 生成 bis(2,4-diacetoxy-5-hexyl-1-phenyl)(2-pyridyl)methane
  参考文献：
  名称：

  Accumulation of hydrogen-bonding and electrostatic binding sites: stabilization of salts in hydroxylic media via intramolecular hydrogen bonding

  摘要：

  Pyridyl-bisresorcinol derivative 1a and dodecyl phosphate (5) form a pyridinium-phosphate salt which is stabilized via hydrogen-bonding interaction between the bisresorcinol moiety and bound phosphate anion. The salt-formation constants (K) are relatively insensitive to solvent polarities; K1a(5) = 1.2 x 10(3) (water-methanol (2:1)), 1.2 x 10(3) (methanol), 1.1 x 10(3) (ethanol), and 6.9 x 10(2) M-1 (2-propanol). On the other hand, the salt formation with 2-picoline (3) as a less crowded reference host takes place with much difficulty and is highly solvent dependent; K3(5) = 2.1 x 10(2) (water-methanol (2:1)), 3.2 x 10 (methanol), 1.6 x 10 (ethanol), and 9.2 (2-propanol). The selectivities K1a(5)/K3(5) thus increase with respect to change in solvents in the order, water-methanol (2:1) (6) < methanol (37) < ethanol (72) < 2-propanol (75). The role of a pair of hydroxyl groups in the bisresorcinol moiety is discussed in terms of intramolecular microsolvation.

  DOI：

  10.1021/jo00026a009
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-己基间苯二酚 在 盐酸 作用下， 以 甲醇 为溶剂， 以72%的产率得到bis(2,4-dihydroxy-5-hexyl-1-phenyl)(2-pyridyl)methane
  参考文献：
  名称：

  Accumulation of hydrogen-bonding and electrostatic binding sites: stabilization of salts in hydroxylic media via intramolecular hydrogen bonding

  摘要：

  Pyridyl-bisresorcinol derivative 1a and dodecyl phosphate (5) form a pyridinium-phosphate salt which is stabilized via hydrogen-bonding interaction between the bisresorcinol moiety and bound phosphate anion. The salt-formation constants (K) are relatively insensitive to solvent polarities; K1a(5) = 1.2 x 10(3) (water-methanol (2:1)), 1.2 x 10(3) (methanol), 1.1 x 10(3) (ethanol), and 6.9 x 10(2) M-1 (2-propanol). On the other hand, the salt formation with 2-picoline (3) as a less crowded reference host takes place with much difficulty and is highly solvent dependent; K3(5) = 2.1 x 10(2) (water-methanol (2:1)), 3.2 x 10 (methanol), 1.6 x 10 (ethanol), and 9.2 (2-propanol). The selectivities K1a(5)/K3(5) thus increase with respect to change in solvents in the order, water-methanol (2:1) (6) < methanol (37) < ethanol (72) < 2-propanol (75). The role of a pair of hydroxyl groups in the bisresorcinol moiety is discussed in terms of intramolecular microsolvation.

  DOI：

  10.1021/jo00026a009