4-(2-甲氧基苯基)苯胺 | 263901-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-甲氧基苯基)苯胺
• 中文别名: 2'-甲氧基-联苯-4-基胺；(2-甲氧基二苯-4-基)胺1HCL
• 英文名称: 2'-Methoxy-biphenyl-4-ylamine
• 英文别名: 2′-methoxy[1,1′-biphenyl]-4-amine；2'-methoxybiphenyl-4-amine；4-(2-methoxyphenyl)aniline；2-methoxy-4'-aminobiphenyl；2'-Methoxy-biphenyl-4-ylamin
• CAS: 263901-48-0
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: VPUUSIRSYXBBJA-UHFFFAOYSA-N

物化性质

• 沸点：
  312.2±17.0 °C(Predicted)
• 密度：
  1.1

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  4-(2-甲氧基苯基)苯胺 在 盐酸 、 ammonium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 24.0h， 生成 5-isoxazoleacetic acid, 3-<3-(aminoiminomethyl)phenyl>-5-<<<2'-methoxy<1,1'-biphenyl>-4-yl>amino>carbonyl>-4,5-dihydro-, methyl ester
  参考文献：
  名称：

  Design and Synthesis of Isoxazoline Derivatives as Factor Xa Inhibitors. 1

  摘要：

  Thrombosis is a major cause of mortality in the industrialized world. Therefore, the prevention of blood coagulation has become a major target for new therapeutic agents. One attractive approach is the inhibition of factor Xa (FXa), the enzyme directly responsible for protbrombin activation. We report a series of novel biaryl-substituted isoxazoline derivatives in which the biaryl moiety was designed to interact with the S-4 aryl-binding domain of the FXa active site. Several of the compounds herein have low nanomolar affinity for FXa, have good in vitro selectivity for FXa, and show potent antithrombotic efficacy in vivo, The three most potent compounds (33, 35, and 37) have inhibition constants for human FXa of 3.9, 2.3, and 0.83 nM, respectively, and ID50's ranging from 0.15 to 0.26 mu mol/kg/h in the rabbit arterio-venous thrombosis model.

  DOI：

  10.1021/jm980405i
• 作为产物：
  描述：

  1-甲氧基-2-(4-硝基苯基)苯 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以99%的产率得到4-(2-甲氧基苯基)苯胺
  参考文献：
  名称：

  Discovery and SAR study of novel dihydroquinoline containing glucocorticoid receptor ligands

  摘要：

  We report the discovery of a novel class of glucocorticoid receptor (GR) ligands based on 1,2-dihydroquinoline molecular scaffold. The compounds exhibit good GR binding affinity and selectivity profile against other nuclear hormone receptors. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.043

文献信息

• Fingerprints of Singlet and Triplet Phenyl Cations
  作者：Micha Slegt、Hermen S. Overkleeft、Gerrit Lodder

  DOI：10.1002/ejoc.200700339

  日期：2007.11

  The photolyses of seven phenyl cation precursors in acetonitrile in the presence of anisole resulted in four distinct product patterns. These patterns are due to the chemoselective and regioselective chemistry of various phenyl cation isomers. This spin-selective chemistry provides a tool with which to fingerprint the singlet/triplet nature of any phenyl cation.(© Wiley-VCH Verlag GmbH & Co. KGaA,

  在苯甲醚存在下，七种苯基阳离子前体在乙腈中的光解产生四种不同的产物模式。这些模式归因于各种苯基阳离子异构体的化学选择性和区域选择性化学。这种自旋选择性化学提供了一种工具，可用于识别任何苯基阳离子的单线态/三线态性质。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2007）
• 3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations
  作者：Jing Tang、Feng Liu、Eva Nagy、Lena Miller、Karen A. Kirby、Daniel J. Wilson、Bulan Wu、Stefan G. Sarafianos、Michael A. Parniak、Zhengqiang Wang

  DOI：10.1021/acs.jmedchem.5b01879

  日期：2016.3.24

  achieve selective RNase H inhibition. Biochemical studies showed the two subtypes with an N-1 methyl group (9 and 10) inhibited RNase H in low micromolar range without siginificantly inhibiting RT polymerase, whereas the N-1 unsubstituted subtype 11 inhibited RNase H in submicromolar range and RT polymerase in low micromolar range. Subtype 11 also exhibited substantially reduced inhibition in the HIV-1

  人类免疫缺陷病毒（HIV）逆转录酶（RT）相关的核糖核酸酶H（RNase H）仍然是未经验证的抗病毒靶标。特异性靶向HIV RNase H的主要挑战来自对RT聚合酶（pol）和整合酶（IN）链转移（ST）抑制作用的普遍缺乏选择性。我们在此报告了三种新颖的3-羟基嘧啶-2,4-二酮（HPD）亚型的合成和生化评估，这些亚型经过精心设计以实现选择性RNase H抑制。生化研究表明，具有N-1甲基的两个亚型（9和10）在低微摩尔范围内抑制RNase H，而未显着抑制RT聚合酶，而N-1未取代的亚型11在亚微摩尔范围内抑制RNase H，在低微摩尔范围内抑制RT聚合酶。亚型11在HIV-1 INST分析中也表现出明显降低的抑制作用，在细胞生存力分析中没有明显的细胞毒性，这表明它可能适合进一步的结构-活性关系（SAR），以鉴定具有抗病毒活性的RNase H抑制剂。
• Organogold(I) Phosphanes in Palladium-Catalyzed Cross-Coupling Reactions in Aqueous Media
  作者：Miguel Peña-López、Luis A. Sarandeses、José Pérez Sestelo

  DOI：10.1002/ejoc.201201720

  日期：2013.5

  Cross-coupling reaction of organogold(I) phosphanes with organic electrophiles in aqueous media has been investigated. Reactions between isolated aryl-, alkenyl-, or alkynylgold(I) phosphanes and aryl halides or triflates, alkenyl halides, and allyl acetates proceed under palladium catalysis conditions at room temperature or 80 °C in water with THF as a co-solvent. The coupling reactions give good yields

  已经研究了有机金 (I) 膦与有机亲电试剂在水性介质中的交叉偶联反应。分离的芳基-、烯基-或炔基金 (I) 膦与芳基卤化物或三氟甲磺酸酯、烯基卤化物和乙酸烯丙酯之间的反应在钯催化条件下在室温或 80 °C 的水中进行，THF 作为共溶剂。偶联反应具有良好的产率，并且具有高度通用性和化学选择性，允许在亲电子试剂中存在游离氨基或羟基。该方法用于制备取代的苯丙氨酸酯，证明金 (I) 有机金属化合物是质子条件下金属催化交叉偶联反应的合适试剂。
• Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant
  作者：Lian-Yan Liao、Kun-Ming Liu、Xin-Fang Duan

  DOI：10.1021/acs.joc.5b01787

  日期：2015.10.16

  reaction of two aryl metal reagents is described. An equivalent amount of two aryl Grignard or lithium reagents, after mediation by an equivalent amount of simple ClTi(OEt)3, was facilely assembled under the catalysis of 1 mol % of CoCl2/10 mol % of DMPU using oxygen. The cross-couplings between various aryl metal reagents, especially between two structurally similar aryl Grignard reagents, proceeded smoothly

  描述了两种芳基金属试剂的首次钴催化的氧化交叉偶联反应。通过简单的将ClTi（OET）等量的两个芳基或格利雅试剂锂等量，调停后3，1摩尔％的氯化钴的催化下轻便组装2使用氧气/ 10％（摩尔）的DMPU。各种芳基金属试剂之间，特别是两种结构相似的芳基格氏试剂之间的交叉偶联，可以平稳，选择性地进行，因此提供了一种构建联芳基化合物的高度通用且有效的方法。
• Facile synthesis of mono-, bis- and tris-aryl-substituted aniline derivatives in aqueous DMF
  作者：Chun Liu、Xiaoxiao Song、Qijian Ni、Jieshan Qiu

  DOI：10.3998/ark.5550190.0013.906

  日期：——

  A facile, efficient and general protocol for synthesizing a series of mono-, bisand tris-arylsubstituted aniline derivatives is described via the Pd(OAc)2-catalyzed aerobic and ligand-free Suzuki reaction of mono-, diand tribromoanilines with aryl boronic acids in aqueous N,Ndimethylformamide (DMF). This is the first example to prepare 2,6-bisaryl-4-nitroanilines and 2,6-bisarylanilines via a palladium-catalyzed

  通过 Pd(OAc)2 催化的单、二和三溴苯胺与芳基硼酸的有氧和无配体 Suzuki 反应，描述了合成一系列单、双和三芳基取代苯胺衍生物的简便、高效和通用的方案。 N,N-二甲基甲酰胺 (DMF) 水溶液。这是通过钯催化的无配体 Suzuki 反应制备 2,6-双芳基-4-硝基苯胺和 2,6-双芳基苯胺的第一个例子。