2-dicyclohexylphosphino-4'-methylaminobiphenyl | 482377-57-1

• 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-4'-methylaminobiphenyl
• 英文别名: [4-(2-Dicyclohexylphosphanylphenyl)phenyl]methanamine；[4-(2-dicyclohexylphosphanylphenyl)phenyl]methanamine
• CAS: 482377-57-1
• 化学式: C₂₅H₃₄NP
• 分子量: 379.525
• InChiKey: SZAANXRWKMLUEP-UHFFFAOYSA-N

物化性质

• 沸点：
  544.4±43.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-dicyclohexylphosphino-4'-methylaminobiphenyl 在 水 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4'-(aminomethyl)-[1,1'-biphenyl]-2-yl)dicyclohexylphosphine oxide
  参考文献：
  名称：

  “点击”树枝状膦：设计，合成，在铃木偶联中的应用以及纳米过滤的回收利用

  摘要：

  Abstractmagnified imageA new synthetic route towards stable molecular‐weight enlarged monodentate phosphine ligands via ‘click’ chemistry was developed. These ligands were applied in the Pd‐catalyzed Suzuki–Miyaura coupling of aryl halides and phenyl boronic acid. The supported systems show very similar activities compared to the unsupported analogues. Moreover, recycling experiments by means of nanofiltration using ceramic nanofiltration membranes demonstrate that these systems can be recovered and reused efficiently.

  DOI：

  10.1002/adsc.200900058
• 作为产物：
  描述：

  2'-溴联苯-4-腈 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 7.0h， 生成 2-dicyclohexylphosphino-4'-methylaminobiphenyl
  参考文献：
  名称：

  Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands

  摘要：

  Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00576-8

文献信息

• A Dual‐Metal‐Catalyzed Sequential Cascade Reaction in an Engineered Protein Cage**
  作者：Paul Ebensperger、Mariia Zmyslia、Philipp Lohner、Judith Braunreuther、Benedikt Deuringer、Anita Becherer、Regine Süss、Anna Fischer、Claudia Jessen‐Trefzer

  DOI：10.1002/anie.202218413

  日期：——

  Inside an artificial protein cage, a dual-metal-tagged guest protein catalyzed a linear, two-step sequential cascade reaction involving deprotection followed by hydroamination. This non-orthogonal tandem catalysis in an encapsulin nanocompartment opens an exciting toolbox for the development of compartmentalized prodrug activation reactions in biological systems.

  在人工蛋白质笼内，双金属标记的客体蛋白质催化了一个线性的、两步连续的级联反应，包括脱保护和加氢胺化。包封蛋白纳米隔室中的这种非正交串联催化打开了一个令人兴奋的工具箱，用于在生物系统中开发隔室化的前药活化反应。
• Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands
  作者：Masato Nishimura、Masato Ueda、Norio Miyaura

  DOI：10.1016/s0040-4020(02)00576-8

  日期：2002.7

  Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.
• ‘Click’ Dendritic Phosphines: Design, Synthesis, Application in Suzuki Coupling, and Recycling by Nanofiltration
  作者：Michèle Janssen、Christian Müller、Dieter Vogt

  DOI：10.1002/adsc.200900058

  日期：2009.2

  Abstractmagnified imageA new synthetic route towards stable molecular‐weight enlarged monodentate phosphine ligands via ‘click’ chemistry was developed. These ligands were applied in the Pd‐catalyzed Suzuki–Miyaura coupling of aryl halides and phenyl boronic acid. The supported systems show very similar activities compared to the unsupported analogues. Moreover, recycling experiments by means of nanofiltration using ceramic nanofiltration membranes demonstrate that these systems can be recovered and reused efficiently.