1-(4-甲氧基苯氧基)-3-硝基苯 | 37984-00-2

• 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: 1-(4-甲氧基苯氧基)-3-硝基苯
• 英文名称: 3-(4-methoxy-phenoxy)nitrobenzene
• 英文别名: 1-(4-methoxyphenoxy)-3-nitrobenzene；4-Methoxy-3'-nitro-diphenylaether；1-methoxy-4-(3-nitro-phenoxy)-benzene；1-Methoxy-4-(3-nitro-phenoxy)-benzol；p-(m-Nitrophenoxy)anisole
• CAS: 37984-00-2
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: CSYDROGXZKHHQE-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  190 °C(Press: 3 Torr)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苯氧基)-3-硝基苯 在 三溴化硼 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.67h， 生成 1-(2-(4-(3-nitrophenoxy)phenoxy)ethyl)pyrrolidine
  参考文献：
  名称：

  Discovery of Dual Target Inhibitors against Cyclooxygenases and Leukotriene A₄ Hydrolyase

  摘要：

  Dual target inhibitors against COX-2. and LTA(4)H were designed by adding functional groups from a marketed COX-2 inhibitor, Nimesulide, to an existing LTA(4)H inhibitor 1-(2-(4-phenoxyphenoxy) ethyl) pyrrolidine. A series of phenoxyphenyl pyrrolidine compounds were synthesized and tested for their inhibition activities using enzyme assays and human whole blood assay. Introduction of small electron withdrawing groups like NO2 and CF3 in the ortho-position of the terminal phenyl ring was found to change the original single target LTA(4)H inhibitor to dual target LTA(4)H and COX-2 inhibitors. Compound 5a and 5m showed dual LTA(4)H and COX-2 inhibition activities in the enzyme assays and the I-EWE assay with IC50 values in the micromolar to submicromolar range. As their activities in HWB assay were comparable to the two starting single target inhibitors, the two compounds are promising for further studies. The strategy used in the current study may be generally applicable to other dual target drug designs.

  DOI：

  10.1021/jm200063s
• 作为产物：
  描述：

  4-碘苯甲醚 在 copper(ll) sulfate pentahydrate 、 水 、 caesium carbonate 、 sodium ascorbate 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 48.5h， 生成 1-(4-甲氧基苯氧基)-3-硝基苯
  参考文献：
  名称：

  Copper and l -sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides

  摘要：

  CuSO4 center dot 5H(2)O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, allcylaryl ethers, and diaryl thioethers were synthesized in high yield. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.066

文献信息

• [EN] SUBSTITUTED TRIAZINONES AS THYROID HORMONE RECEPTOR AGONISTS<br/>[FR] TRIAZINONES SUBSTITUÉES EN TANT QU'AGONISTES DU RÉCEPTEUR DE L'HORMONE THYROÏDIENNE
  申请人：ECCOGENE SHANGHAI CO LTD

  公开号：WO2021143706A1

  公开（公告）日：2021-07-22

  The application relates to a compound of Formula (I') or (I), or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, stereoisomer, or tautomer thereof, which modulates the activity of thyroid hormone receptors, a pharmaceutical composition comprising a compound of Formula (I') or (I), and a method of treating or preventing a disease or disorder regulated by thyroid hormone.

  该申请涉及式(I')或(I)的化合物，或其药物可接受的盐、水合物、溶剂化物、前药、立体异构体或互变异构体，其可调节甲状腺激素受体的活性，包含式(I')或(I)的化合物的药物组合物，以及用于治疗或预防由甲状腺激素调节的疾病或失调的方法。
• Hydrolysis of Diaryliodonium Salts
  作者：Marjorie C. Caserio、Donald L. Glusker、John D. Roberts

  DOI：10.1021/ja01511a019

  日期：1959.1

  The products of hydrolysis of some unsymmetrically substituted diphenyliodonium salts to phenols and aryl iodides have been identified and their distributions determined. The direction of cleavage has been found to be insensitive to the nature of the substituents, the solvent, catalysts, and the nature of the associated anion, fluoride, fluoroborate, p-toluenesulfonate or trifluoroacetate. A rate study

  一些不对称取代的二苯基碘盐水解为苯酚和芳基碘的产物已被鉴定并确定了它们的分布。已发现裂解方向对取代基的性质、溶剂、催化剂和相关阴离子、氟化物、氟硼酸盐、对甲苯磺酸盐或三氟乙酸盐的性质不敏感。一项速率研究表明，水解是一个复杂的反应，当使用二恶烷-水作为溶剂时，它被酸阻滞并被铜亚铜和氧气催化。讨论了可能的机制。
• Dimethylaminomethylphosphonic Acid Derivatives-Promoted CuI-Catalyzed Synthesis of Aryl Ethers
  作者：Hua Fu、Ying Jin、Jinyong Liu、Yingwu Yin、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2006-941587

  日期：2006.6

  An inexpensive and efficient catalyst system for synthesis of aryl ethers has been developed by using 20 mol% CuI as the catalyst, 30 mol% dimethylaminomethylphosphonic acid derivatives as the new ligands, K2CO3 as the base and toluene as the ­solvent. This is the first example using aminophosphonates as the ligands for Ullmann ether coupling reaction.

  一种廉价且高效的催化剂系统用于合成芳基醚，使用20 mol%的CuI作为催化剂，30 mol%的二甲氨基甲基膦酸衍生物作为新配体，K2CO3作为碱，甲苯作为溶剂。这是首次将氨基膦酸酯作为Ullmann醚偶联反应的配体。
• Highly Efficient Copper-Catalyzed O-Arylation Using Readily Available (<i>S</i>)-<i>N</i>-Methylpyrrolidine-2-Carboxamide as the Ligand
  作者：Hua Fu、Xianghao Liu、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2007-1000878

  日期：2008.1

  A highly efficient and readily available catalyst system for O-arylation of various phenols using CuI and (S)-N-methylpyrrolidine-2-carboxamide (Pro-NHMe) was developed. The reaction is widely applicable to the synthesis of diaryl ethers

  开发了一种高效且易获取的催化剂体系，用于使用CuI和(S)-N-甲基吡咯烷-2-羧酰胺（Pro-NHMe）对各种酚进行O-芳基化。该反应广泛适用于二芳醚的合成。
• Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
  作者：Tanmoy Maity、Debraj Saha、Soma Das、Susmita Bhunia、Subratanath Koner

  DOI：10.1016/j.catcom.2014.09.006

  日期：2015.1

  A highly porous Zn-based iso-reticular metal–organic framework (IRMOF-3) has been selected for covalent modification. Pyridine-2-aldehyde has been used to decorate the free amine group of IRMOF-3 in the porous matrix. Schiff base moiety thus generated has been availed to anchor copper(II) ions to prepare the desired catalyst that catalyzes O-arylation reactions heterogeneously under mild reaction conditions

  选择了高度多孔的锌基等网状金属-有机骨架（IRMOF-3）进行共价修饰。吡啶-2-醛已用于修饰多孔基质中IRMOF-3的游离胺基。这样产生的席夫碱部分已被用于锚定铜（II）离子以制备所需的催化剂，该催化剂在温和的反应条件下非均相地催化O-芳基化反应。当各种底物与α和β-萘酚进行O-芳基化反应时，多孔催化剂在产物中表现出尺寸选择性。