3-(4-bromophenyl)-5-(4-(decyloxy)phenyl)isoxazole | 1133827-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-bromophenyl)-5-(4-(decyloxy)phenyl)isoxazole
• 英文别名: 3-(4-Bromophenyl)-5-(4-decoxyphenyl)-1,2-oxazole
• CAS: 1133827-45-8
• 化学式: C₂₅H₃₀BrNO₂
• 分子量: 456.423
• InChiKey: NAYLRMKDBPZIRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吩噻嗪 、 3-(4-bromophenyl)-5-(4-(decyloxy)phenyl)isoxazole 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 5-(4-Decoxyphenyl)-3-(4-phenothiazin-10-ylphenyl)-1,2-oxazole
  参考文献：
  名称：

  Büchwald-Hartwig Reaction Applied to Synthesis of New Luminescent Liquid Crystal Triarylamines Derived from Isoxazoles

  摘要：

  The present work describes the synthesis and characterization of novel series of triarylamines isoxazoles (TAA) addressed to the organic photovoltaic materials. Diarylisoxazoles were synthesized by sequential [3+2] 1,3-dipolar cycloaddition reaction between arylnitrile oxides and selected arylalkenes followed by MnO2-oxidation. Isoxazoles were coupled to diarylamines by Buchwald-Hartwig reaction to afford desired compounds 6a-k. Some TAA display liquid-crystalline behaviour and UV-Vis absorption and fluorescence emission were analysed for all samples of TAA 6a-k.

  DOI：

  10.1080/15421406.2015.1030982
• 作为产物：
  描述：

  4-bromobenzaldehyde oxime 在 盐酸 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 82.0h， 生成 3-(4-bromophenyl)-5-(4-(decyloxy)phenyl)isoxazole
  参考文献：
  名称：

  Büchwald-Hartwig Reaction Applied to Synthesis of New Luminescent Liquid Crystal Triarylamines Derived from Isoxazoles

  摘要：

  The present work describes the synthesis and characterization of novel series of triarylamines isoxazoles (TAA) addressed to the organic photovoltaic materials. Diarylisoxazoles were synthesized by sequential [3+2] 1,3-dipolar cycloaddition reaction between arylnitrile oxides and selected arylalkenes followed by MnO2-oxidation. Isoxazoles were coupled to diarylamines by Buchwald-Hartwig reaction to afford desired compounds 6a-k. Some TAA display liquid-crystalline behaviour and UV-Vis absorption and fluorescence emission were analysed for all samples of TAA 6a-k.

  DOI：

  10.1080/15421406.2015.1030982

文献信息

• 1,3-Dipolar cycloaddition reaction applied to synthesis of new unsymmetric liquid crystal compounds-based isoxazole
  作者：André A. Vieira、Fernando R. Bryk、Gilmar Conte、Adailton J. Bortoluzzi、Hugo Gallardo

  DOI：10.1016/j.tetlet.2008.12.021

  日期：2009.2

  ring compounds exhibited mesomorphism. Smectic C, smectic A, and nematic phases were observed by optical microscopy and DSC analysis. The yield of these reactions varied from moderate to excellent (47–93%). The structure of the rigid core was investigated by single crystal X-ray diffraction, which confirmed the regioselectivity of the [3+2] dipolar cycloaddition reaction.

  在这项研究中，开发了一种区域选择性，简单和通用的铜（I）催化方法，用于制备基于非对称3,5-二取代异恶唑的一系列液晶。使用不同的取代的氯肟和苯基乙炔，进行了1,3-偶极环加成反应。还合成了在刚性核中包含异恶唑环和三键的第二系列。由Sonogashira交叉偶联从3-（4-溴苯基）-5-（4-（癸氧基）苯基）异恶唑制备新的液晶化合物。异恶唑环化合物的所有衍生物均表现出同构。通过光学显微镜和DSC分析观察到近晶相C，近晶相A和向列相。这些反应的产率从中度到优异（47-93％）不等。