3-((4-chlorophenyl)amino)phenol | 66282-78-8

• 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-chlorophenyl)amino)phenol
• 英文别名: 3-(4-chloroanilino)phenol
• CAS: 66282-78-8
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: GSHBBDLSLCDLCP-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  364.7±22.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  2

反应信息

• 作为产物：
  描述：

  4-溴氯苯 、 3-氨基苯酚 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93%的产率得到3-((4-chlorophenyl)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

• Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides
  作者：Martins S. Oderinde、Natalie H. Jones、Antoine Juneau、Mathieu Frenette、Brian Aquila、Sharon Tentarelli、Daniel W. Robbins、Jeffrey W. Johannes

  DOI：10.1002/anie.201604429

  日期：2016.10.10

  visible‐light‐promoted iridium photoredox and nickel dual‐catalyzed cross‐coupling procedure for the formation C−N bonds has been developed. With this method, various aryl amines were chemoselectively cross‐coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C−N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more

  已经开发了可见光促进的铱光氧化还原和镍双催化交叉偶联过程，以形成CN键。通过这种方法，将各种芳基胺与电子和空间上不同的芳基碘化物和溴化物进行化学选择性交联，以形成相应的C-N键，这在制药工业中引起了极大的兴趣。发现芳基碘化物是更有效的亲电子偶联伴侣。偶联反应是在室温下进行的，没有严格排除分子氧，因此使这种新开发的Ir-photoredox / Ni双催化过程非常温和且操作简单。
• Novel alpha adrenergic agents
  申请人：——

  公开号：US20030092741A1

  公开（公告）日：2003-05-15

  Aspects of the present invention are directed towards compounds of Formula I for the treatment of human erectile disorders including erectile dysfunction in men. 1 wherein: R 1 is hydrogen, halo, hydroxy, nitro, cyano, phenyl, trifluoromethyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, carboxy, amino, cyclohexyl, C 1 -C 6 alkylamino, or (C 1 -C 6 alkyl) 2 amino; R 2 is hydrogen, halo, hydroxy, nitro, cyano, trifluoromethyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, carboxy, amino, C 1 -C 6 alkylamino, or (C 1 -C 6 alkyl) 2 amino; R 3 is a group of the formula 2 R 4 is hydrogen or C 1 -C 6 alkyl; R 5 is hydrogen, halo, hydroxy, nitro, cyano, phenyl, trifluoromethyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, carboxy, amino, C 1 -C 6 alkylamino, or (C 1 -C 6 alkyl) 2 amino; and R 6 is hydrogen, halo, hydroxy, nitro, cyano, trifluoromethyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, carboxy, amino, C 1 -C 6 alkylamino, or (C 1 -C 6 alkyl) 2 amino; or pharmaceutically acceptable salts thereof

  本发明涉及一种用于治疗人类勃起障碍的化合物的公式I，包括男性勃起功能障碍。其中：R1为氢、卤素、羟基、硝基、氰基、苯基、三氟甲基、C1-C6烷基、C1-C6烷氧基、羧基、氨基、环己基、C1-C6烷基氨基或（C1-C6烷基）2氨基；R2为氢、卤素、羟基、硝基、氰基、三氟甲基、C1-C6烷基、C1-C6烷氧基、羧基、氨基、C1-C6烷基氨基或（C1-C6烷基）2氨基；R3为式2的基团；R4为氢或C1-C6烷基；R5为氢、卤素、羟基、硝基、氰基、苯基、三氟甲基、C1-C6烷基、C1-C6烷氧基、羧基、氨基、C1-C6烷基氨基或（C1-C6烷基）2氨基；R6为氢、卤素、羟基、硝基、氰基、三氟甲基、C1-C6烷基、C1-C6烷氧基、羧基、氨基、C1-C6烷基氨基或（C1-C6烷基）2氨基；或其药用盐。
• Chemoselective Chan-Lam and reductive nitroarene coupling of boronic acid using an octahedral Ni-DMAP complex as catalyst
  作者：Hrishikesh Talukdar、Daisy Gogoi、Prodeep Phukan

  DOI：10.1016/j.tet.2023.133251

  日期：2023.2

  cross coupling and reductive nitroarene coupling using boronic acid as coupling partner. Reaction of amines, thiols, azides, and tosyl azides with boronic acids could be achieved in presence of 10 mol % of the catalyst in methanol at 80 °C without using extra base. The current protocol is highly selective for primary amines in presence of secondary amines, thiols and phenols. Reductive coupling of a

  开发了一种八面体 Ni-DMAP 配合物作为C- N 和C- S 交叉偶联和使用硼酸作为偶联剂的还原性硝基芳烃偶联的催化剂。胺、硫醇、叠氮化物和甲苯磺酰叠氮化物与硼酸的反应可以在 10 mol% 的催化剂存在下于 80 °C 的甲醇中实现，无需使用额外的碱。目前的协议在仲胺、硫醇和酚存在下对伯胺具有高度选择性。使用相同的催化剂也成功地实现了一系列硝基芳烃和硼酸的还原偶联。
• Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound
  作者：George W. Kabalka、Bryan J. Musolino

  DOI：10.3987/com-14-s(k)18

  日期：——

  This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%(1) Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.
• DE515208
  申请人：——

  公开号：——

  公开（公告）日：——