2-amino-4-(4'-hexyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester | 1397205-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(4'-hexyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester
• CAS: 1397205-62-7
• 化学式: C₂₄H₂₇NO₃S
• 分子量: 409.549
• InChiKey: JHPZBMASQVRDOI-UHFFFAOYSA-N

物化性质

• 熔点：
  120-124 °C
• 沸点：
  574.4±50.0 °C(predicted)
• 密度：
  1.149±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-(4-hexyloxy-phenyl)-vinyl]-benzoyl chloride 、 2-amino-4-(4'-hexyloxy-biphenyl-4-yl)-thiophene-3-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 以42%的产率得到4-(4'-hexyloxy-biphenyl-4-yl)-2-{4-[2-(4-hexyloxy-phenyl)-vinyl]-benzoylamino}-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
• 作为产物：
  描述：

  1-(4'-hexyloxy-biphenyl-4-yl)-ethanone 在 吗啉 、 三甲基硅乙酸酯 、 ammonium acetate 、 sulfur 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 2-amino-4-(4'-hexyloxy-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