3-(4-methoxyphenoxy)aniline | 105903-05-7

• 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-methoxyphenoxy)aniline
• 英文别名: 3-(4-Methoxy-phenoxy)-anilin
• CAS: 105903-05-7
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: YWHQDIKEXSFCGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  355.5±22.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenoxy)aniline 在 氢碘酸 、 溶剂黄146 、 三乙胺 作用下， 生成 3-(4-Hydroxiphenoxi)-trifluormethansulfonanilid
  参考文献：
  名称：

  DE2118190

  摘要：

  公开号：
• 作为产物：
  描述：

  4-碘苯甲醚 、 3-氨基苯酚 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以77%的产率得到3-(4-methoxyphenoxy)aniline
  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

• CuI/Oxalamide Catalyzed Couplings of (Hetero)aryl Chlorides and Phenols for Diaryl Ether Formation
  作者：Mengyang Fan、Wei Zhou、Yongwen Jiang、Dawei Ma

  DOI：10.1002/anie.201601035

  日期：2016.5.17

  Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N‐aryl‐N′‐alkyl‐substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N‐aryl‐N′‐alkyl‐substituted oxalamides are more effective ligands than bis(N‐aryl)‐substituted oxalamides. A wide range of electron‐rich and electron‐poor aryl and heteroaryl chlorides gave the corresponding

  CuI与N-芳基-N'-烷基取代的草酰胺配体结合可以有效地促进（杂）芳基氯与苯酚之间的偶联，使其在120°C下顺利进行。在此过程中，N-芳基-N'-烷基取代的草酰胺比双（N-芳基）-取代的草酰胺更有效。各种各样的富电子和贫电子的芳基和杂芳基氯化物都能以良好的收率得到相应的偶联产物。富电子酚和有限范围的贫电子酚实现了令人满意的转化。低至1.5 mol％的催化剂和配体负载量足以满足其中某些反应的放大规模。
• Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings
  作者：Yuntong Zhai、Xiaofei Chen、Wei Zhou、Mengyang Fan、Yisheng Lai、Dawei Ma

  DOI：10.1021/acs.joc.7b00493

  日期：2017.5.5

  Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2–2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether

  通过在CuI / N，N'-双（2-苯基苯基）草酰胺（BPPO）或CuI / N-（2-苯基苯基）-N'-苄基草酰胺的催化下偶联酚和（杂）芳基卤化物来形成二芳基（PPBO）在90°C下使用DMF或MeCN作为溶剂。完全转化仅需要0.2–2 mol％的CuI和配体，这代表了通常的Cu /配体催化的二芳基醚形成的最低催化负载量。
• AMIDE DERIVATIVE
  申请人：TOHOKU UNIVERSITY

  公开号：US20160368860A1

  公开（公告）日：2016-12-22

  The present invention provides a useful medicament for the treatment and/or prophylaxis of a disease associated with the enhancement of OPN production including cancer, which comprises a compound of formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , m, n, p, X, and Y are as defined in the specification, a pharmaceutically acceptable salt thereof.

  本发明提供了一种用于治疗和/或预防与增加OPN产生相关的疾病，包括癌症的有用药物，其包括以下公式的化合物：其中R1、R2、R3、R4、R5、R6、R7、m、n、p、X和Y如规范中定义，其药学上可接受的盐。
• AMIDE DERIVATIVES
  申请人：Tohoku University

  公开号：EP3112343A1

  公开（公告）日：2017-01-04

  The present invention provides a useful medicament for the treatment and/or prophylaxis of a disease associated with the enhancement of OPN production including cancer, which comprises a compound of formula: wherein R1, R2, R3, R4, R5, R6, R7, m, n, p, X, and Y are as defined in the specification, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种用于治疗和/或预防与 OPN 生成增强有关的疾病（包括癌症）的有用药物，它包括一种式化合物： 其中 R1、R2、R3、R4、R5、R6、R7、m、n、p、X 和 Y 如说明书中所定义，或其药学上可接受的盐。
• Amide derivative
  申请人：TOHOKU UNIVERSITY

  公开号：US11040937B2

  公开（公告）日：2021-06-22

  The present invention provides a useful medicament for the treatment and/or prophylaxis of a disease associated with the enhancement of OPN production including cancer, which comprises a compound of formula: wherein R1, R2, R3, R4, R5, R6, R7, m, n, p, X, and Y are as defined in the specification, a pharmaceutically acceptable salt thereof.

  本发明提供了一种用于治疗和/或预防与 OPN 生成增强有关的疾病（包括癌症）的有用药物，它包括一种式化合物： 其中R1、R2、R3、R4、R5、R6、R7、m、n、p、X和Y如说明书中所定义，其为药学上可接受的盐。