2-氟-5-硝基联苯 | 103977-87-3

• 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: 2-氟-5-硝基联苯
• 英文名称: 2-fluoro-5-nitro-1-phenylbenzene
• 英文别名: 2-fluoro-5-nitrobiphenyl；4-fluoro-3-phenylnitrobenzene；2-Fluoro-5-nitro-biphenyl；1-fluoro-4-nitro-2-phenylbenzene
• CAS: 103977-87-3
• 化学式: C₁₂H₈FNO₂
• 分子量: 217.199
• InChiKey: BLGDHUAUKNHHIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氟-5-硝基联苯 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.58h， 生成
  参考文献：
  名称：

  Dialkylimidazole inhibitors of Trypanosoma cruzi sterol 14α-demethylase as anti-Chagas disease agents

  摘要：

  New dialkylimidazole based sterol 14 alpha-demethylase inhibitors were prepared and tested as potential anti-Trypanosoma cruzi agents. Previous studies had identified compound 2 as the most potent and selective inhibitor against parasite cultures. In addition, animal studies had demonstrated that compound 2 is highly efficacious in the acute model of the disease. However, compound 2 has a high molecular weight and high hydrophobicity, issues addressed here. Systematic modifications were carried out at four positions on the scaffold and several inhibitors were identified which are highly potent (EC50 <1 nM)against T. cruzi in culture. The halogenated derivatives 36j, 36k, and 36p, display excellent activity against T. cruzi amastigotes, with reduced molecular weight and lipophilicity, and exhibit suitable physicochemical properties for an oral drug candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.015
• 作为产物：
  描述：

  2-氟-5-硝基苯胺 、 亚硝酸异戊酯 以 苯 为溶剂， 以49%的产率得到2-氟-5-硝基联苯
  参考文献：
  名称：

  Antibiotic derivatives of

  摘要：

  具有抗菌活性的1-取代-6-氟-7-芳基-(8-氟)-1,4-二氢喹啉-4-酮3-羧酸是通过将相应的烷基1-取代-6-氟-7-溴-(8-氟)-1,4-二氢喹啉-4-酮-3-羧酸酯与芳基金属化合物反应，并水解形成的酯来制备的。

  公开号：

  US04623650A1

文献信息

• Synthesis of Alkyl-Aryl Ethers by Copper-catalyzed Etherization Reactions of Aryl Fluorides with Tetraalkylammonium Bromides and H2O
  作者：Feng Wang、Boxiao Tang、Yexiang Xie、Jinheng Li

  DOI：10.1002/cjoc.201090383

  日期：2010.11

  Synthesis of alkyl aryl ethers via copper‐catalyzed etherizations of electron‐deficient aryl fluorides with quaternary ammonium bromides and water has been developed. In the presence of Cu(OAc)2, POPh3 (L4) and Cs2CO3, a variety of electron‐deficient aryl fluorides underwent the reaction with quaternary ammonium bromides and H2O in moderate to good yields. The mechanism was also discussed.

  已经开发了通过缺电子的芳基氟化物与溴化季铵和水的铜催化醚化反应来合成烷基芳基醚的方法。在存在Cu（OAc）2，POPh 3（L4）和Cs 2 CO 3的情况下，各种缺电子的芳基氟化物与季铵溴化物和H 2 O反应的产率中等至良好。还讨论了该机制。
• Silver-Catalyzed Arylation of (Hetero)arenes by Oxidative Decarboxylation of Aromatic Carboxylic Acids
  作者：Jian Kan、Shijun Huang、Jin Lin、Min Zhang、Weiping Su

  DOI：10.1002/anie.201408630

  日期：2015.2.9

  arylation of heteroarenes by oxidative decarboxylation of aromatic carboxylic acids. To address this challenge, the silver‐catalyzed intermolecular Minisci reaction of aromatic carboxylic acids was developed. With an inexpensive silver salt as a catalyst, this new reaction enables a variety of aromatic carboxylic acids to undergo decarboxylative coupling with electron‐deficient arenes or heteroarenes regardless

  Minisci反应的长期挑战是通过芳族羧酸的氧化脱羧实现杂芳基的芳基化。为了应对这一挑战，开发了银催化的芳香族羧酸分子间Minisci反应。用廉价的银盐作为催化剂，这种新的反应可以实现各种芳族羧酸的经历脱羧耦合用缺电子的芳烃或杂芳烃不管取代基上的芳族羧酸的位置，因此消除了对需要邻-取代的芳族羧酸，这是以前报道的方法的局限性。
• Oxidizing hair coloring agents containing 2,5-diamino-1-phenylbenzene derivatives and novel 2,5-diamino-1-phenylbenzene derivatives
  申请人：Wella Aktiengesellschaft

  公开号：US06500213B1

  公开（公告）日：2002-12-31

  The object of the present patent application are agents for the oxidative coloring of keratin fibers, particularly hair, based on a developer-coupler combination, characterized in that they contain as the developer at least one 2,5-diamino-1-phenylbenzene derivative of general formula and novel 2,5-diamino-1-phenylbenzene derivatives of formula (I) wherein at least one of the R1 to R10 radicals is different from hydrogen.

  本专利申请的对象是用于氧化染色角蛋白纤维，特别是头发的剂，基于发展剂-偶联剂组合，其特征在于它们包含作为发展剂至少一种通式的2,5-二氨基-1-苯基苯衍生物，并且具有通式(I)的新型2,5-二氨基-1-苯基苯衍生物，其中R1至R10中至少有一个基团不同于氢。
• A strategy for ortho-phenylenediamine synthesis via dearomative-rearomative coupling of nitrobenzenes and amines
  作者：Raquel Sánchez-Bento、Baptiste Roure、Josep Llaveria、Alessandro Ruffoni、Daniele Leonori

  DOI：10.1016/j.chempr.2023.10.008

  日期：2023.12

  Mechanistically, this process capitalizes on the conversion of nitrobenzenes into the corresponding single nitrenes, which undergo a series of N-insertion, electrocyclic ring expansion, amine addition, and electrocyclic ring contraction en route to the ortho-phenylenediamines.

  邻位-苯二胺是具有两个邻位N-取代基的芳香族分子，与生物活性材料的开发。这些衍生物目前是由邻-卤代硝基苯通过多步合成序列制备的。在这里，我们报告了一种概念上不同的方法，其中硝基苯和胺可以直接转化为邻-苯二胺，而不需要邻位-卤化并进行逐步合成操作。该策略在简单的蓝光照射下发生，并引入了另一种逆合成策略，其中胺偶联伴侣“似乎”取代了转变为邻位的硝基邻位位置，同时在一锅法中被还原和酰胺化。从机理上讲，该过程利用硝基苯转化为相应的单一氮烯，并经历一系列N-插入、电环扩环、胺加成、和电环收缩在形成邻位-苯二胺的过程中。
• Discovery of TD-4306, a long-acting β2-agonist for the treatment of asthma and COPD
  作者：R. Murray McKinnell、Uwe Klein、Martin S. Linsell、Edmund J. Moran、Matthew B. Nodwell、Juergen W. Pfeiffer、G. Roger Thomas、Cecile Yu、John R. Jacobsen

  DOI：10.1016/j.bmcl.2014.04.095

  日期：2014.7

  A multivalent approach focused on amine-based secondary binding groups was applied to the discovery of long-acting inhaled beta(2)-agonists. Addition of amine moieties to the neutral secondary binding group of an existing beta(2)-agonist series was found to provide improved in vivo efficacy, but also led to the formation of biologically active aldehyde metabolites which were viewed as a risk for the development of these compounds. Structural simplification of the scaffold and blocking the site of metabolism to prevent aldehyde formation afforded a potent series of dibasic beta(2)-agonists with improved duration of action relative to their monobasic analogs. Additional optimization led to the discovery of 29 (TD-4306), a potent and selective beta(2)-agonist with potential for once-daily dosing. (C) 2014 Elsevier Ltd. All rights reserved.