2-(bis(4-methoxyphenyl)amino)phenol | 1198118-05-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(bis(4-methoxyphenyl)amino)phenol
• 英文别名: 2-[Bis(4-methoxyphenyl)amino]phenol；2-(4-methoxy-N-(4-methoxyphenyl)anilino)phenol
• CAS: 1198118-05-6
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: IYNHGHOKLFNILT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(bis(4-methoxyphenyl)amino)phenol 在 吡啶 、 (S)-1-[(RP)-2-(二环己基膦基)二茂铁]乙基二环己基膦 、 palladium diacetate 、 caesium carbonate 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-methoxy-9-(4-methoxyphenyl)carbazole
  参考文献：
  名称：

  钯催化 2-（二芳基氨基）苯基三氟甲磺酸酯直接 CH 芳基化合成 N-芳基咔唑

  摘要：

  检查了一系列 2-（二芳基氨基）苯基三氟甲磺酸酯的钯催化直接芳基化。三氟甲磺酸酯首先通过 CuI 催化的氨基苯酚和芳基碘化物的芳基胺化以中等至良好的产率合成，然后是所得三芳基苯酚的三氟甲磺酸酯化。如果使用 Josiphos 作为支持配体，由此获得的 2-（二芳基氨基）苯基三氟甲磺酸酯在 Pd 催化下直接进行 C-H 芳基化，以优异的产率提供相应的 N-芳基咔唑。

  DOI：

  10.1002/ejoc.201601467
• 作为产物：
  描述：

  4-碘苯甲醚 、 2-氨基苯酚 在 copper(l) iodide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以74%的产率得到2-(bis(4-methoxyphenyl)amino)phenol
  参考文献：
  名称：

  铜催化直接合成二苯胺和三苯胺：2-氨基苯酚的显着加速作用

  摘要：

  利用 2-氨基苯酚的显着加速作用，我们开发了一种用于选择性合成二苯胺和三苯胺的铜催化系统。此外，N-和O-芳基化可以在2-氨基苯酚和硝基芳基卤化物之间的偶联反应中实现。

  DOI：

  10.1002/ejoc.201001113

文献信息

• Synthesis of triphenylamines via ligand-free selective ring-opening of benzoxazoles or benzothiazoles under superparamagnetic nanoparticle catalysis
  作者：Oanh T. K. Nguyen、Long T. Nguyen、Nhu K. Truong、Viet D. Nguyen、Anh T. Nguyen、Nhan T. H. Le、Dung T. Le、Nam T. S. Phan

  DOI：10.1039/c7ra06168d

  日期：——

  CuFe2O4 superparamagnetic nanoparticles were utilized as an effective recyclable heterogeneous catalyst for the synthesis of triphenylamines via the ligand-free selective ring-opening reaction of benzoxazoles or benzothiazoles with iodoarenes. The nano CuFe2O4 demonstrated noticeably higher catalytic efficiency than a series of homogeneous catalysts and heterogeneous catalysts. It was possible to separate

  CuFe 2 O 4超顺磁性纳米粒子被用作有效的可循环异构催化剂，用于通过苯并恶唑或苯并噻唑与碘代芳烃的无配体选择性开环反应合成三苯胺。与一系列均相催化剂和非均相催化剂相比，纳米CuFe 2 O 4表现出明显更高的催化效率。可以分离出纳米CuFe 2 O 4通过使用磁体，回收的催化剂可重复使用多次，同时可保持其活性。据我们所知，这是苯并恶唑转化过程中非均相催化的第一个例子，而苯并噻唑向三苯胺的转化尚未见报道。
• Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols
  作者：Debabrata Maiti、Stephen L. Buchwald

  DOI：10.1021/ja9081815

  日期：2009.12.2

  O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N'-dimethyl-1,2-cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.
• Copper-Catalyzed Selective Arylations of Benzoxazoles with Aryl Iodides
  作者：Donghae Kim、Kwangho Yoo、Se Eun Kim、Hee Jin Cho、Junseong Lee、Youngjo Kim、Min Kim

  DOI：10.1021/acs.joc.5b00019

  日期：2015.4.3

  A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.
• Heterogeneous Copper–Catalyzed Synthesis of S–Arylated 2-Aminothiophenols via Ring Opening of Benzothiazoles and C–S Coupling using Aryl Halides
  作者：Hironao Sajiki、Tomohiro Ichikawa、Tomohiro Matsuo、Takumu Tachikawa、Yoshinari Sawama、Yasunari Monguchi

  DOI：10.3987/com-18-s(t)55

  日期：——

  Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl iodides or aryl bromides in the presence of lithium tert-butoxide in aqueous 2-propanol.