2-{4-[2-(4-hexyloxy-phenyl)-vinyl]-benzoylamino}-4-(4'-octyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester | 1397205-88-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-{4-[2-(4-hexyloxy-phenyl)-vinyl]-benzoylamino}-4-(4'-octyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester
• 英文别名: methyl 2-[[4-[(E)-2-(4-hexoxyphenyl)ethenyl]benzoyl]amino]-4-[4-(4-octoxyphenyl)phenyl]thiophene-3-carboxylate
• CAS: 1397205-88-7
• 化学式: C₄₇H₅₃NO₅S
• 分子量: 744.008
• InChiKey: BNOOJBZQKGZBIY-CCEZHUSRSA-N

物化性质

• 熔点：
  165-167 °C
• 沸点：
  804.7±65.0 °C(predicted)
• 密度：
  1.134±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氰基联苯酚 在 吗啉 、 4-二甲氨基吡啶 、 三甲基硅乙酸酯 、 ammonium acetate 、 potassium carbonate 、 sulfur 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 79.67h， 生成 2-{4-[2-(4-hexyloxy-phenyl)-vinyl]-benzoylamino}-4-(4'-octyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and study of new rod-like mesogens containing 2-aminothiophene unit

  摘要：

  We present a synthesis and mesomorphic properties of a new series of rod-like mesogens. All the compounds possess a substituted 2-aminothiophene unit as a main element in the structure attached to a stilbene moiety with a terminal alkyloxy chain (OR1, OR2 where R-1=CnH2n+1, R-2=CmH2m+1; n, m ranging from 6 to 12). The synthesis of alkyloxybiphenyl substituted 2-aminothiophenes was carried out by the Gewald reaction and the appropriate reaction conditions were investigated. The liquid-crystalline properties were studied via polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction. These materials exhibit nematic and/or smectic A phases. The influence of structural changes (variation in alkyloxy chain length and symmetry of the molecule) on mesogenic behaviour is discussed. Evaluation of UV-vis, fluorescent and electrochemical properties are also included. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.075

文献信息

• Synthesis and study of new rod-like mesogens containing 2-aminothiophene unit
  作者：Zita Puterová、Jerzy Romiszewski、Jozef Mieczkowski、Ewa Gorecka

  DOI：10.1016/j.tet.2012.07.075

  日期：2012.9

  We present a synthesis and mesomorphic properties of a new series of rod-like mesogens. All the compounds possess a substituted 2-aminothiophene unit as a main element in the structure attached to a stilbene moiety with a terminal alkyloxy chain (OR1, OR2 where R-1=CnH2n+1, R-2=CmH2m+1; n, m ranging from 6 to 12). The synthesis of alkyloxybiphenyl substituted 2-aminothiophenes was carried out by the Gewald reaction and the appropriate reaction conditions were investigated. The liquid-crystalline properties were studied via polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction. These materials exhibit nematic and/or smectic A phases. The influence of structural changes (variation in alkyloxy chain length and symmetry of the molecule) on mesogenic behaviour is discussed. Evaluation of UV-vis, fluorescent and electrochemical properties are also included. (C) 2012 Elsevier Ltd. All rights reserved.