6-bromo-1-(4-methoxyphenyl)naphthalen-2-ol | 1216834-15-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-1-(4-methoxyphenyl)naphthalen-2-ol
• CAS: 1216834-15-9
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: CLNWOWRRTOAYQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-bromo-1-diazonaphthalen-2(1H)-one 、 苯甲醚 在 iron(III) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以84%的产率得到6-bromo-1-(4-methoxyphenyl)naphthalen-2-ol
  参考文献：
  名称：

  Fe(OTf)3催化1-重氮萘-2(1H)-酮直接芳基化反应区域选择性构建功能化联芳醇及其荧光特性

  摘要：

  已经开发了一种通过 Fe(OTf)3 催化 1-diazonaphthalen-2(1H)-ones 与芳烃的直接芳基化来构建功能化联芳醇的简便有效的协议。这种方法以中等至良好的产率提供了多种 1-arylnaphthalen-2-ols。这种方法也已应用于合成具有生物学意义的多环芳烃取代和杂芳基取代 naphthalen-2-ols。带有蒽支架的合成化合物可用作克隆细胞共聚焦成像的潜在荧光生物标志物。

  DOI：

  10.1002/ejoc.201701533

文献信息

• DHTP Ligands for the Highly Ortho-Selective, Palladium-Catalyzed Cross-Coupling of Dihaloarenes with Grignard Reagents: A Conformational Approach for Catalyst Improvement
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1002/anie.200905544

  日期：2010.1.18

  Palladium catalysts bearing dihydroxyterphenylphosphine ligands (such as 1) are reported for the ortho‐selective cross‐coupling of Grignard reagents and dihaloarenes. The second hydroxy group onto the terphenylphosphine ligand dramatically improved the catalytic efficiency and expanded the scope of the reaction.

  据报道，带有二羟基三苯膦配体（如1）的钯催化剂可用于格氏试剂和二卤代芳烃的邻位选择性交叉偶联。三苯基膦配体上的第二个羟基大大提高了催化效率并扩大了反应范围。
• Hydroxylated terphenylphosphine ligands for palladium-catalyzed ortho-selective cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents
  作者：Shunpei Ishikawa、Kei Manabe

  DOI：10.1016/j.tet.2011.09.013

  日期：2011.12

  p-Terphenylphosphines bearing one or two hydroxy groups were used as ligands to palladium in the cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents. High ortho-selectivity that cannot be achieved using other phosphine ligands was observed. ortho-Preference was also observed in competitive cross-coupling reactions of two substrates. A significant effect of the concentration of the Grignard reagent on the ortho-selectivity was observed, when the hydroxylated terphenylphosphines were used. Kinetic studies on this effect showed that high concentrations of the Grignard reagent retard the cross-coupling reaction only at the para-position, but not at the ortho-position. (C) 2011 Elsevier Ltd. All rights reserved.