4-[2-(1-Butylpyridin-4-ylidene)ethylidene]-2,6-dimethoxycyclohexa-2,5-dien-1-one | 355404-31-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(1-Butylpyridin-4-ylidene)ethylidene]-2,6-dimethoxycyclohexa-2,5-dien-1-one
• CAS: 355404-31-8
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: JWPZXZQUBQBOFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-butyl-4-[2-(3,5-dimethoxy-4-hydroxyphenyl)ethenyl]piridinium chloride 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以88%的产率得到4-[2-(1-Butylpyridin-4-ylidene)ethylidene]-2,6-dimethoxycyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Synthesis, spectroscopic and structural elucidation of 1-butyl-4-[2-(3,5-dimethoxy-4-hydroxyphenyl)ethenyl)]pyridinium chloride tetrahydrate

  摘要：

  The novel chloride salt of 1-butyl-4-[2-(4-hydroxyphenyl)ethenyl)]pyridine (1), has been synthesized as the tetrahydrate and its structure and properties elucidated in detail spectroscopically, thermally and structurally, using single crystal X-ray diffraction, linear-polarized solid-state IR-spectroscopy, UV-spectroscopy and mass spectrometry. Quantum chemical calculations were performed with a view to supporting and explaining the experimental structural and spectroscopic data. The compound (1) crystallizes in triclinic P (1) over bar space group and its unit cell contains two independent 1-butyl-4-[2-(3,5-dimethoxy4-hydroxyphenyl)ethenyl)]pyridinium] cations, differing with respect to the butyl chain torsion angle for which values of 80.0(9)degrees and 173.6(3)degrees are observed. The cations and anions are joined into infinite layers, formed by two different dimers and including solvent molecules. Hydrogen bonds OH center dot center dot center dot OH2 (2.814 angstrom), HOH center dot center dot center dot O(CH3)(2.960 angstrom), OH center dot center dot center dot Cl (2.967 angstrom). HOH center dot center dot center dot Cl- (3.034, 3.188, 3.161 and 3.062 angstrom) and HCH center dot center dot center dot OH2 (2.772 angstrom) are observed. For first time in the literature, we are reporting the crystal structure of the dye with the syring-fragment in the molecule. The spectroscopic properties of the novel compound are compared and with those of the corresponding quinoide form (2). Both the forms (1) and (2) are characterized by 21 and 140 nm solvatochromic effects depending of the type of the solvent. The UV-spectroscopic data in solution confirm the formation of classical H-aggregates in polar protic solvent mixture. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2009.09.020