4-butoxy-4'-methoxybiphenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-butoxy-4'-methoxybiphenyl
• 英文别名: 4-butoxy-4’-methoxy-1,1’-biphenyl；4-butoxy-4'-methoxy-1,1'-biphenyl；1-Butoxy-4-(4-methoxyphenyl)benzene；1-butoxy-4-(4-methoxyphenyl)benzene
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: HUCKYXRWAGLQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-butoxy-4'-methoxybiphenyl 在 3,3-二甲基-1-丁烯 、 双三甲基硅氧基甲基硅烷 、 C₃₄H₅₁AlN₃P₂Rh 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 17.0h， 生成 4-联苯硼酸新戊二醇酯
  参考文献：
  名称：

  铑-铝异双金属配合物催化芳醚的选择性C-O键还原和硼化

  摘要：

  我们报道了带有X型PAlP钳形配体的铑配合物催化C-O键的催化还原和硼化。我们已经基于反应中间体的表征和氘标记实验揭示了反应机理。值得注意的是，这种新颖的催化体系显示出与空间位阻相关的化学选择性，这不同于传统的基于镍的催化剂，并提出了一种通过异双金属催化选择性激活C-O键的新策略。

  DOI：

  10.1021/jacs.1c03038
• 作为产物：
  描述：

  4-溴苯酚 在 bis(η3-allyl-μ-chloropalladium(II)) potassium carbonate 、 三苯基氧化膦 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 49.0h， 生成 4-butoxy-4'-methoxybiphenyl
  参考文献：
  名称：

  Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates

  摘要：

  The palladium-catalyzed cross-coupling reaction of potassium (4-methoxyphenyl) dimethylsilanolate (K(+)1(-)) with aryl bromides has been demonstrated using triphenylphosphine oxide as a stabilizing ligand. Unsymmetrical biaryls can be prepared from a variety of aryl bromides in good yield with short reaction times. Qualitative kinetic studies compared effects of different phosphine oxides on the rate of cross-coupling and established the beneficial effect of these ligands in the reaction of electron-rich arylsilanolates. The improved yield and reproducibility of the cross-coupling of several bromides was demonstrated by direct comparison of reactions performed with and without triphenylphosphine oxide under non-rigorous exclusion of oxygen. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.017

文献信息

• A Polystyrene‐Cross‐Linking Tricyclohexylphosphine: Synthesis, Characterization and Applications to Pd‐Catalyzed Cross‐Coupling Reactions of Aryl Chlorides
  作者：Junya Arashima、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1002/asia.201801651

  日期：2019.2

  polystyrene‐cross‐linking tricyclohexylphosphine (PS‐TCP) was synthesized through radical emulsion polymerization of 4‐tert‐butylstyrene as a monomer and tris(trans‐4‐styrylcyclohexyl)phosphine as a threefold cross‐linker. The PS‐TCP showed enhanced ligand performance compared to the corresponding polystyrene‐triphenylphosphine hybrid PS‐TPP and tricyclohexylphosphine in Pd‐catalyzed Suzuki–Miyaura and Buchwald–Hartwig

  聚苯乙烯交联三环己基膦（PS-TCP）是通过4-叔丁基苯乙烯作为单体和三（反-4-苯乙烯基环己基）膦作为三重交联剂的自由基乳液聚合而合成的。与相应的聚苯乙烯-三苯膦杂化体PS-TPP和三环己基膦相比，PS-TCP在Pd催化的Suzuki-Miyaura和Buchwald-Hartwig芳基氯化物反应中表现出增强的配体性能。
• Selective C–O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium–Aluminum Heterobimetallic Complex
  作者：Rin Seki、Naofumi Hara、Teruhiko Saito、Yoshiaki Nakao

  DOI：10.1021/jacs.1c03038

  日期：2021.5.5

  We report the catalytic reduction of a C–O bond and the borylation by a rhodium complex bearing an X-type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts

  我们报道了带有X型PAlP钳形配体的铑配合物催化C-O键的催化还原和硼化。我们已经基于反应中间体的表征和氘标记实验揭示了反应机理。值得注意的是，这种新颖的催化体系显示出与空间位阻相关的化学选择性，这不同于传统的基于镍的催化剂，并提出了一种通过异双金属催化选择性激活C-O键的新策略。
• Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates
  作者：Scott E. Denmark、Russell C. Smith、Steven A. Tymonko

  DOI：10.1016/j.tet.2007.02.017

  日期：2007.6

  The palladium-catalyzed cross-coupling reaction of potassium (4-methoxyphenyl) dimethylsilanolate (K(+)1(-)) with aryl bromides has been demonstrated using triphenylphosphine oxide as a stabilizing ligand. Unsymmetrical biaryls can be prepared from a variety of aryl bromides in good yield with short reaction times. Qualitative kinetic studies compared effects of different phosphine oxides on the rate of cross-coupling and established the beneficial effect of these ligands in the reaction of electron-rich arylsilanolates. The improved yield and reproducibility of the cross-coupling of several bromides was demonstrated by direct comparison of reactions performed with and without triphenylphosphine oxide under non-rigorous exclusion of oxygen. (C) 2007 Elsevier Ltd. All rights reserved.