5-叔丁基-2-硝基苯胺 | 142564-53-2

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 5-叔丁基-2-硝基苯胺
• 英文名称: 5-(tert-butyl)-2-nitroaniline
• 英文别名: 5-tert-Butyl-2-nitroaniline；5-tert-butyl-2-nitro-aniline；4-Nitro-3-amino-1-tert.-butyl-benzol；5-tert-Butyl-2-nitro-anilin；5-tert-butyl-2-nitro-phenylamine
• CAS: 142564-53-2
• 化学式: C₁₀H₁₄N₂O₂
• mdl: MFCD01463636
• 分子量: 194.233
• InChiKey: SXKXVEBWNNCSSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-叔丁基-2-硝基苯胺 在 盐酸 、 tin(ll) chloride 作用下， 生成 4-叔丁基苯-1,2-二胺
  参考文献：
  名称：

  Gelzer, Chemische Berichte, 1888, vol. 21, p. 2956

  摘要：

  DOI：
• 作为产物：
  描述：

  3-叔丁基苯胺 在 potassium carbonate 、 potassium nitrate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 5-叔丁基-2-硝基苯胺
  参考文献：
  名称：

  Synthesis of Heterocyclic Thiosulfonates

  摘要：

  [formula: see text] A simple synthesis of heterocyclic thiosulfonates containing indole, indoline, benzoimidazole, and quinoxaline rings is described. The synthesis of these thiosulfonates involves the preparation of the appropriately substituted thiols followed by sulfonylation to give thiosulfonates. The corresponding thiols were prepared in a simple and efficient manner by using a thiocyanation reaction either prior to heterocycle ring formation or after heterocycle ring formation. These thiosulfonates were coupled successfully to the 5,6-dihydropyran-2-one ring to give products that showed excellent HIV protease activity.

  DOI：

  10.1021/ol0056170

文献信息

• HIV protease inhibitors
  申请人：Warner-Lambert Company

  公开号：US06528510B1

  公开（公告）日：2003-03-04

  The present invention relates to novel dihydropyrones with tethered heterocycles having improved pharmacologic properties which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The dihydropyrones are useful in the development of therapies for the treatment of viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of the dihydropyrones and intermediates useful in the preparation of the final compounds.

  本发明涉及具有改进药理特性的新型带有连环杂环的二氢吡喃，能有效抑制HIV天冬氨酸蛋白酶，阻断HIV的感染性。这些二氢吡喃在开发治疗病毒感染和疾病，包括艾滋病的疗法方面是有用的。本发明还涉及合成这些二氢吡喃的方法，以及在制备最终化合物中有用的中间体。
• Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-a]quinoxalines
  作者：Huanhuan Liu、Feiyu Zhou、Wen Luo、Yuxin Chen、Chenyang Zhang、Chen Ma

  DOI：10.1039/c7ob01688c

  日期：——

  A practical and concise protocol for the efficient synthesis of pyrrolo[1,2-a]quinoxalines from readily available α-amino acids and 2-(1H-pyrrol-1-yl)anilines under transition metal-free conditions has been established. This protocol, which includes the formation of new C–C and C–N bonds, features a wide substrate scope with a broad range of functional group tolerance.

  建立了一种实用且简洁的方案，可在无过渡金属的条件下从容易获得的α-氨基酸和2-（1 H-吡咯-1-基）苯胺有效合成吡咯并[1,2- a ]喹喔啉。该协议包括新的C–C和C–N键的形成，具有广泛的底物范围和广泛的官能团耐受性。
• Phenoxazine: A Privileged Scaffold for Radical-Trapping Antioxidants
  作者：Luke A. Farmer、Evan A. Haidasz、Markus Griesser、Derek A. Pratt

  DOI：10.1021/acs.joc.7b02025

  日期：2017.10.6

  H-atom transfer kinetics and stability to one-electron oxidation results from the ability of the bridging oxygen atom in phenoxazine to serve as both a π-electron donor to stabilize the aminyl radical and σ-electron acceptor to destabilize the aminyl radical cation. Perhaps most excitingly, phenoxazines have “non-classical” RTA activity, where they trap >2 peroxyl radicals each, at ambient temperatures

  二苯胺广泛用于保护石油衍生产品免遭自氧化。它们作为自由基捕获抗氧化剂（RTA）的功效取决于快速H原子转移动力学和对过氧化物物种对单电子氧化的稳定性之间的平衡。H-原子的转移和单电子氧化都可以通过供电子性取代基（如吩噻嗪中的S-原子，另一类重要的RTA）进行取代来增强。本文中，我们报告了我们对结构相关但基本被忽略的吩恶嗪的RTA活性进行研究的结果。我们发现，取代的吩恶嗪的H原子转移反应性遵循极好的Evans-Polanyi相关性，范围为k inh = 4.5×10 6 M –1 s –1和3-CN，7-NO 2-吩恶嗪的N–H BDE = 77.4 kcal mol –1至k inh = 6.6×10 8 M –1 s –1和3 –––––– H BDE = 71.8 kcal mol –1。 7-（OMe）2-吩恶嗪（37°C）。后一种化合物的反应活性是有史以来报道的所有RTA中最大的，并
• A convenient copper-catalyzed direct amination of nitroarenes with O-alkylhydroxylamines
  作者：Shinzo Seko、Kunihito Miyake、Norio Kawamura

  DOI：10.1039/a901537j

  日期：——

  O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields. ortho- or para-Amination with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c–f, 14 and 22g.

  O-烷基羟胺，尤其是O-甲基羟胺，在强碱和铜催化剂的存在下与硝基芳烃反应，生成氨基硝基芳烃，且产率良好。相对于硝基组，发生邻位或对位氨基化反应，在某些情况下，邻位氨基化产物优先获得。对于3-取代的硝基苯，其中取代基带有孤对电子，氨基化优先发生在2位，生成空间位阻最大的3c–f、14和22g。
• Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen
  作者：Mieczyslaw Makosza、Maciej Bialecki

  DOI：10.1021/jo00044a002

  日期：1992.8

  Nitroarenes react with sulfenamides RSNH2 in the presence of strong bases to give p- and o-nitro-anilines.