1-bromo-2-cyano-6-methyl-4-octyloxybenzene | 601479-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-bromo-2-cyano-6-methyl-4-octyloxybenzene
• 英文别名: 2-Bromo-3-methyl-5-octoxybenzonitrile
• CAS: 601479-05-4
• 化学式: C₁₆H₂₂BrNO
• 分子量: 324.261
• InChiKey: PSUSMEQLGJUIMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-2-cyano-6-methyl-4-octyloxybenzene 、 苯硼酸 在 1,1'-双(二苯基膦)二茂铁 、 barium hydroxide octahydrate 、 palladium diacetate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 48.0h， 以40%的产率得到2-cyano-6-methyl-4-octyloxy-1,1'-biphenyl
  参考文献：
  名称：

  Application of the Suzuki Reaction as the Key Step in the Synthesis of a Novel Atropisomeric Biphenyl Derivative for Use as a Liquid Crystal Dopant

  摘要：

  A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.

  DOI：

  10.1021/jo034652s
• 作为产物：
  描述：

  3,5-二甲基苯酚 在 4 A molecular sieve 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 溴 、 氧气 、 potassium carbonate 、 溶剂黄146 、 copper(l) chloride 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 64.0h， 生成 1-bromo-2-cyano-6-methyl-4-octyloxybenzene
  参考文献：
  名称：

  Application of the Suzuki Reaction as the Key Step in the Synthesis of a Novel Atropisomeric Biphenyl Derivative for Use as a Liquid Crystal Dopant

  摘要：

  A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.

  DOI：

  10.1021/jo034652s

文献信息

• Application of the Suzuki Reaction as the Key Step in the Synthesis of a Novel Atropisomeric Biphenyl Derivative for Use as a Liquid Crystal Dopant
  作者：Andrew N. Cammidge、Karen V. L. Crépy

  DOI：10.1021/jo034652s

  日期：2003.8.1

  A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.