4-[(E)-2-(4-decyloxy-phenyl)-vinyl]-benzoic acid methyl ester | 1397205-73-0

• 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: 4-[(E)-2-(4-decyloxy-phenyl)-vinyl]-benzoic acid methyl ester
• 英文别名: methyl 4-[(E)-2-(4-decanoxyphenyl)ethenyl]benzoate
• CAS: 1397205-73-0
• 化学式: C₂₆H₃₄O₃
• 分子量: 394.554
• InChiKey: JOXHTKMNACXTAP-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-(4-decyloxy-phenyl)-vinyl]-benzoic acid methyl ester 在 4-二甲氨基吡啶 、 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 2-{4-[2-(4-decyloxy-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
• 作为产物：
  描述：

  对羟基苯甲醛 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-[(E)-2-(4-decyloxy-phenyl)-vinyl]-benzoic 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

• Insights into the reaction of trans-diarylethenes with thionyl chloride: a practical synthesis of chlorobenzo[b]thiophenes
  作者：Jie Han、Qiong Wang、Xiaoyong Chang、Yuxin Liu、Yanmei Wang、Jiben Meng

  DOI：10.1016/j.tet.2011.09.060

  日期：2011.11

  found for the first time to be also converted into cholobenzo[b]thiophenes under treatment of thionyl chloride. The chemical transformations have been mechanistically rationalized and successfully applied to a one-pot synthesis of novel fluorescent liquid crystalline compounds containing benzo[b]thiophene and 1,3,4-oxadiazole units. Their spectroscopic and mesogenic behaviours are also described.

  已经研究了各种反式-1，2-二芳基醚与亚硫酰氯的反应性。在温和条件下，所有底物都可以轻松获得中等收率的3-氯苯并[ b ]噻吩和少量的苏-和赤-1,2-二氯-1,2-二芳基乙烷。首次发现苯环上带有甲氧基的1,2-二氯-1，2-二芳基乙烷的非对映异构体在亚硫酰氯的处理下也被转化为氯苯并[ b ]噻吩。化学转化已经机械化合理化，并成功地应用于一锅合成含有苯并[ b]的新型荧光液晶化合物。]噻吩和1,3,4-恶二唑单元。还描述了它们的光谱和介晶行为。
• Alkoxy/halostyryl benzoic acids: Synthesis, crystal structure, and study of mesomorphic and photophysical properties
  作者：Khushi Muhammad、M. Khawar Rauf、M. Nawaz Tahir、Shahid Hameed

  DOI：10.1080/15421406.2017.1328215

  日期：2017.6.13

  Alkoxy/halostyrylbenzoic acids were synthesized and evaluated for their mesomorphic and photophysical properties. The trans geometry of the molecules was established by the presence of large coupling constants in H-1-NMR spectra and confirmed further by X-ray diffraction (XRD) analysis of two of the compounds. The straight-chain acids were found fairly stable showing first sign of decomposition above 290 degrees C. The enantiotropic mesophases could only be studied in acids with seven or more methylene groups in the alkoxy chain. Textures of nematic and smectic phases were exhibited by these acids under polarizing optical microscope. Photophysical behavior of the compounds in solution was also investigated.