3-((4-fluorophenyl)amino)phenol | 65250-80-8

• 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: 3-((4-fluorophenyl)amino)phenol
• 英文别名: 3-(4-Fluorophenylamino)phenol；3-(4-fluoroanilino)phenol
• CAS: 65250-80-8
• 化学式: C₁₂H₁₀FNO
• 分子量: 203.216
• InChiKey: LXYGWTJJXYKWGH-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C
• 沸点：
  333.9±22.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基苯酚 、 对溴氟苯 在 chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll) 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以90%的产率得到3-((4-fluorophenyl)amino)phenol
  参考文献：
  名称：

  Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols

  摘要：

  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.

  DOI：

  10.1021/ja9081815

文献信息

• <i>N</i>,<i>N</i>′-Dimethylurea as an efficient ligand for the synthesis of pharma-relevant motifs through Chan–Lam cross-coupling strategy
  作者：Rakhee Saikia、Sanghamitra Das、Arzu Almin、Abhijit Mahanta、Bipul Sarma、Ashim J. Thakur、Utpal Bora

  DOI：10.1039/d3ob00176h

  日期：——

  is introduced as a ligand to aid the Chan–Lam N-arylation of primary amides, amines, and 3-aminophenols with arylboronic acids and its ester derivative as the arylating associate. The developed methodology is catalyzed by Cu and its in situ complexation with DMU brings about efficient synthesis of N-arylated anilines, 3-aminophenols, and primary amides in moderate to good yields (50–90%). The [Cu2(OAc)4(DMU)2]

  N , N ′-二甲基脲 (DMU) 作为配体引入，以辅助 Chan-Lam伯酰胺、胺和 3-氨基苯酚与芳基硼酸及其酯衍生物作为芳基化缔合物的 N-芳基化。开发的方法由 Cu 催化，其与 DMU 的原位络合以中等至良好的产率 (50-90%) 高效合成N-芳基化苯胺、3-氨基苯酚和伯酰胺。合成了[Cu 2 (OAc) 4 (DMU) 2 ] 络合物，并通过单晶结构解析对其进行了表征。该催化剂价格便宜，无需预先合成金属络合物，对 N2 具有化学选择性3-氨基苯酚的芳基化，适用于伯酰胺的单芳基化。该方法的合成效用在两种活性药物成分 (API) 的后修饰中进行了测试。所开发的催化系统扩展了N , N'-二甲基脲作为廉价且通用的 Cu 催化助剂的范围。