1-(4''-methyl-[1,1';4',1'']terphenyl-4-yl)-ethanone

• 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''-methyl-[1,1';4',1'']terphenyl-4-yl)-ethanone
• 英文别名: 1-(4-Methyl-[1,1':4',1'']terphenyl-4''-yl)ethanone；1-[4-[4-(4-methylphenyl)phenyl]phenyl]ethanone
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: AFSAVLDGVZEMED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-乙酰基苯硼酸 在 palladium diacetate 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(4''-methyl-[1,1';4',1'']terphenyl-4-yl)-ethanone
  参考文献：
  名称：

  A Practical and General Synthesis of Unsymmetrical Terphenyls

  摘要：

  [GRAPHICS]A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.

  DOI：

  10.1021/jo701308b

文献信息

• Regioselective routes to orthogonally-substituted aromatic MIDA boronates
  作者：Adam J. Close、Paul Kemmitt、S. Mark Roe、John Spencer

  DOI：10.1039/c6ob01141a

  日期：——

  A series of tetrasubstituted aromatics has been synthesized, many of which are based on elaborated N-methyliminodiacetic acid (MIDA)-boronates. A sequence employing nitration, bromination, stepwise Suzuki–Miyaura (SM) coupling with a boronic acid, then base-mediated unmasking of the boronic acid from the MIDA-boronate and a second SM-coupling has led to our desired, mainly 1,2,4,5-substituted tetrasubstituted

  已经合成了一系列的四取代的芳族化合物，其中许多是基于精制的N-甲基亚氨基二乙酸（MIDA）-硼酸酯。采用硝化，溴化，逐步将Suzuki-Miyaura（SM）与硼酸偶联，然后通过碱基介导的MIDA-硼酸酯对硼酸的脱掩蔽和第二次SM偶联的序列导致我们所需的主要是1,2 ，4,5-取代的四取代的芳族靶标。
• SYSTEM FOR CONTROLLING THE REACTIVITY OF BORONIC ACIDS
  申请人：Burke Martin D.

  公开号：US20090030238A1

  公开（公告）日：2009-01-29

  A protected organoboronic acid includes a boron having an sp 3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp 3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

  一种受保护的有机硼酸包括具有sp3杂化的硼，与硼键合的构象刚性保护基团，以及通过硼-碳键与硼键合的有机基团。执行化学反应的方法包括将受保护的有机硼酸与试剂接触，受保护的有机硼酸包括具有sp3杂化的硼，与硼键合的构象刚性保护基团，以及通过硼-碳键与硼键合的有机基团。有机基团在化学上被转化，而硼没有在化学上被转化。
• An Improved Suzuki-Miyaura Cross-Coupling Reaction for the Synthesis of Fluorine-Substituted 3-Biaryl-1-ferrocenyl-2-propen-1-one
  作者：Qing-bao Song、Ru-xiang Lin、Ming-yu Teng、Jie Zhang、Chun-an Ma

  DOI：10.1055/s-2005-921748

  日期：——

  We studied the Pd(0)-catalyzed Suzuki-Miyaura cross-coupling reaction and obtained an improved procedure with shorter reaction times and higher conversions.

  我们研究了 Pd（0）催化的铃木-宫浦交叉偶联反应，并获得了一种反应时间更短、转化率更高的改进程序。
• A Practical and General Synthesis of Unsymmetrical Terphenyls
  作者：Jose M. Antelo Miguez、Luis Angel Adrio、Antonio Sousa-Pedrares、Jose M. Vila、King Kuok (Mimi) Hii

  DOI：10.1021/jo701308b

  日期：2007.9.1

  [GRAPHICS]A synthetic procedure was developed that enables sequential chemoselective Suzuki-Miyaura cross-coupling of chlorobromobenzene with arylboronic acids. The first coupling is achieved at room temperature using a ligandless palladium catalyst. The chlorobiaryl product can then be subjected directly to the second coupling, facilitated by the SPhos ligand. Using this methodology, parallel synthesis of 32 unsymmetrical o-, m-, and p-terphenyl compounds was accomplished in good to excellent overall yields.