3-(4-bromophenyl)-5-(4-(tert-butoxy)phenyl)isoxazole | 1349699-49-5

• 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-(tert-butoxy)phenyl)isoxazole
• 英文别名: 5-(4-tert-butoxyphenyl)-3-(4-bromophenyl)isoxazole；3-(4-Bromophenyl)-5-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1,2-oxazole；3-(4-bromophenyl)-5-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1,2-oxazole
• CAS: 1349699-49-5
• 化学式: C₁₉H₁₈BrNO₂
• 分子量: 372.261
• InChiKey: OGNXISFLRJJWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  3-(4-bromophenyl)-5-(4-(tert-butoxy)phenyl)isoxazole 在 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 30.0h， 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
• 作为产物：
  描述：

  4-bromobenzaldehyde oxime 在 盐酸 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 52.0h， 生成 3-(4-bromophenyl)-5-(4-(tert-butoxy)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

• 3,5-diarylisoxazoles: A New Entry to Soft Crystal Phase
  作者：Rafaela R. da Rosa、Irwing S. Brose、Guilherme D. Vilela、Aloir A. Merlo

  DOI：10.1080/15421406.2015.1030975

  日期：2015.5.3

  This work describes the synthesis and characterization of a new liquid-crystalline compounds based on isoxazoles. Classical synthetic methodologies were employed in the preparation of this compounds, and the [3+2] 1,3-dipolar cycloaddition was the key step to prepare isoxazolines as precursors to isoxazoles. The structural and thermal characterization was performed using H-1 and C-13 NMR techniques, polarized-light optical microscopy and differential scanning calorimetry. Compounds 7a-e displayed the SmA mesophase. Soft crystal phase (CrE) was observed for compounds 7a and 7b containing chlorine and bromine atoms. For 7e containing a nitro group crystal phases below SmA mesophase were also observed.
• Expeditious preparation of isoxazoles from Δ2-isoxazolines as advanced intermediates for functional materials
  作者：Guilherme D. Vilela、Rafaela R. da Rosa、Paulo H. Schneider、Ivan H. Bechtold、Juliana Eccher、Aloir A. Merlo

  DOI：10.1016/j.tetlet.2011.09.122

  日期：2011.12

  A collection of isoxazoles derivatives has been efficiently synthesized in three steps. The oximation reaction of aldehydes followed by nitrile oxide [3+2] 1,3-dipolar cycloaddition and MnO2-oxidation reaction furnished the title compounds which were purified by simple filtration on celite (R). (C) 2011 Elsevier Ltd. All rights reserved.
• Büchwald-Hartwig Reaction Applied to Synthesis of New Luminescent Liquid Crystal Triarylamines Derived from Isoxazoles
  作者：G. D. Vilela、T. H. M. Fernandes、S. M. Kelly、A. A. Merlo

  DOI：10.1080/15421406.2015.1030982

  日期：2015.5.3

  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.