2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid | 869060-84-4

• 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: 2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid
• 英文别名: 2'-(dicyclohexylphosphino)-biphenyl-4-carboxylic acid；2'-(dicyclohexylphosphino)biphenyl-4-carboxylic acid；2'-(Dicyclohexylphosphino)-[1,1'-biphenyl]-4-carboxylic acid；4-(2-dicyclohexylphosphanylphenyl)benzoic acid
• CAS: 869060-84-4
• 化学式: C₂₅H₃₁O₂P
• 分子量: 394.494
• InChiKey: KVKIOVSCIPOCAV-UHFFFAOYSA-N

物化性质

• 沸点：
  574.0±43.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid 、 五氟苯酚 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到pentafluorophenyl 2-(dicyclohexylphosphino)biphenyl-4'-carboxylate
  参考文献：
  名称：

  Synthesis of an amidosulfonate-tagged biphenyl phosphine and its application in the Suzuki–Miyaura reaction affording biphenyl-substituted amino acids in water

  摘要：

  An amidosulfonate-tagged phosphinobiphenyl, viz triethylammonium 2-(dicyclohexylphosphino)-4'-{[(sulfonatomethyl)amino]carbonyl}biphenyl(3), was prepared in two steps from 2-(dicyclohexylphosphino) biphenyl-4'-carboxylic acid and fully characterized including the crystal structure determination. As a highly polar phosphine ligand, compound 3 was employed in the Pd-catalyzed Suzuki-Miyaura cross-coupling of N-Boc protected 4-bromo and 4-chlorophenylalanine with aromatic boronic acids to afford the corresponding biphenyls in aqueous N,N-dimethylformamide or pure water. The coupling was demonstrated to proceed very well and without the loss of the Boc protecting group when the bromo-substituted substrate is reacted in the presence of 1 mol.% of Pd/3 catalyst in water at 40 degrees C. Reactions with boronic acids bearing electron-withdrawing substituents and, mainly, those with the less reactive chlorophenylalanine substrate required slightly higher reaction temperature and more catalyst to achieve similar results. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.01.020
• 作为产物：
  描述：

  2'-溴联苯-4-腈 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid
  参考文献：
  名称：

  聚合物支持的芳基二环己基膦在芳烃与芳基硼酸的Suzuki-Miyaura反应中的高效回收

  摘要：

  已经开发了聚合物负载的芳基二环己基膦的合成。这些配体的催化性能已在芳基氯与芳基硼酸的Suzuki-Miyaura交叉偶联反应中得到证明。关于催化剂的再循环，基于共聚物聚乙二醇/聚苯乙烯的配体显示出非常高的活性，该活性在6次运行中得以维持。

  DOI：

  10.1002/adsc.200606130

文献信息

• Efficient aqueous-phase Suzuki coupling of activated aryl chlorides with arylboronic acids using d-glucosamine-based dicyclohexylarylphosphine
  作者：Anzhelika Konovets、Alexandra Penciu、Eric Framery、Nathalie Percina、Catherine Goux-Henry、Denis Sinou

  DOI：10.1016/j.tetlet.2005.03.049

  日期：2005.5

  of a new d-glucosamine-based dicyclohexylarylphosphine has been developed. The catalytic performance of this neutral ligand is demonstrated in the Suzuki–Miyaura cross-coupling reaction between several arylboronic acids and aryl or heteroaryl chlorides.

  已经开发了新的基于d-葡糖胺的二环己基芳基膦的合成。几种芳基硼酸与芳基或杂芳基氯化物之间的Suzuki-Miyaura交叉偶联反应证明了这种中性配体的催化性能。