1-(4-(2,6-dimethylphenoxy)phenyl)ethanone | 22100-59-0

• 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: 1-(4-(2,6-dimethylphenoxy)phenyl)ethanone
• 英文别名: 2.6-Dimethyl-1-<4-acetyl-phenoxy>-benzol；2.6-Dimethyl-1-(4-acetyl-phenoxy)-benzol；1-[4-(2,6-Dimethylphenoxy)phenyl]ethanone
• CAS: 22100-59-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: NUUJHQFUYCAEAV-UHFFFAOYSA-N

物化性质

• 沸点：
  350.9±30.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-二甲基苯酚 、 4-乙酰基苯硼酸 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以81%的产率得到1-(4-(2,6-dimethylphenoxy)phenyl)ethanone
  参考文献：
  名称：

  Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound

  摘要：

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.

  DOI：

  10.3987/com-14-s(k)18

文献信息

• Copper promoted synthesis of diaryl ethers
  作者：Rajshekhar Ghosh、Ashoka G. Samuelson

  DOI：10.1039/b401179a

  日期：——

  An efficient protocol using copper based reagents for the coupling of aryl halides with phenols to generate diaryl ethers is described. A copper(I) complex, [Cu(CH3CN)4]ClO4, or the readily available copper(II) source, CuCO3·Cu(OH)2·H2O (in combination with potassium phosphate), can be used. Aryl halides and phenols with different steric and electronic demands have been used to assess the efficiency of the procedure. The latter source of copper gives better yields under all conditions.

  文中描述了一种利用基于铜的试剂实现芳基卤与酚偶联生成二芳基醚的高效协议。可以使用铜(I)配合物，例如[Cu(CH3CN)4]ClO4，或者易于获得的铜(II)源，即铜碳酸盐·氢氧化铜·水（结合磷酸钾）。根据不同的立体和电子需求，使用不同类型的芳基卤和酚来评估该过程的效率。在所有条件下，后一种铜源能够提供更好的产率。
• Metal ions and complexes in organic reactions. Part VII. Copper-promoted hydrogen transfer from aromatic donors to halides
  作者：R. G. R. Bacon、O. J. Stewart

  DOI：10.1039/j39690000301

  日期：——

  substitution by the reductants, and (in the case of o-bromonitrobenzene) with a small amount of Ullmann-type coupling of the halide. Copper(I) oxide or the metal were the most effective of the copper species examined, and both dissolved during reaction. Unsaturated substituents, particularly o-NO2, greatly enhanced reducibility. α-Bromo-ketones readily underwent similar reduction. Fission occurred in the

  铜促进的氢从各种芳族供体向芳基溴的转移，例如在约170°的2,4,6-可力丁或二甲基乙酰胺中，导致还原性取代，ArBr → ArH（高达约80％），有时与还原剂的亲核取代，以及（在邻溴硝基苯的情况下）与少量卤化物的乌尔曼型偶联。氧化铜（I）或金属是所检查的铜种类中最有效的，并且在反应过程中均溶解。不饱和取代基，特别是o -NO 2，大大提高了还原性。α-溴酮很容易经历类似的还原。裂变发生在o的SCN组-硝基苯硫氰酸酯。
• Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound
  作者：George W. Kabalka、Bryan J. Musolino

  DOI：10.3987/com-14-s(k)18

  日期：——

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.