N-(2-羟基-5-硝基苯基)乙酰胺 | 97-60-9

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: N-(2-羟基-5-硝基苯基)乙酰胺
• 英文名称: 2-acetamido-4-nitrophenol
• 英文别名: N-(2-hydroxy-5-nitrophenyl)acetamide；2-Acetamino-4-nitrophenol
• CAS: 97-60-9
• 化学式: C₈H₈N₂O₄
• mdl: MFCD00466540
• 分子量: 196.163
• InChiKey: GFHYFPARONGSCD-UHFFFAOYSA-N

物化性质

• 保留指数：
  2111

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 储存条件：
  2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  N-(2-羟基-5-硝基苯基)乙酰胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 N-(5-氨基-2-羟基苯基)乙酰胺
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033
• 作为产物：
  描述：

  2,4-二硝基酚 在 ammonium sulfide 作用下， 生成 N-(2-羟基-5-硝基苯基)乙酰胺
  参考文献：
  名称：

  Lindemann; Romanoff, Journal fur praktische Chemie (Leipzig 1954), 1929, vol. <2>122, p. 215,220,225

  摘要：

  DOI：

文献信息

• Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Brønsted Acidic NO₂⁺ Generation
  作者：Kevin A. Juárez-Ornelas、J. Oscar C. Jiménez-Halla、Terumasa Kato、César R. Solorio-Alvarado、Keiji Maruoka

  DOI：10.1021/acs.orglett.8b04141

  日期：2019.3.1

  The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Brønsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT)

  使用碘基苯作为基于碘（III）和硝酸铝作为硝基基团来源的有机催化剂，开发了用于苯酚亲电硝化的第一个催化程序。该原子经济方案发生在温和的，非布朗斯台德酸性和开放式烧瓶反应条件下，具有宽泛的官能团耐受性，包括多个杂环。（SMD：MeCN）Mo8-HX /（LANLo8 + f，6-311 + G *）水平的密度泛函理论（DFT）计算表明反应通过阳离子途径进行，该途径有效地产生了NO 2 +离子，从而是中性条件下的硝化物种。
• Amine derivatives, processes for producing them and a use of them as
  申请人：C&C Research Labs.

  公开号：US06057358A1

  公开（公告）日：2000-05-02

  Novel amine derivatives of the following general formula (I): ##STR1## (wherein) A may denote --(CH.sub.2)--O--, --(CH.sub.2).sub.2 --O--, or --(CH.sub.2).sub.2 --NH--; B may denote --(CH.sub.2).sub.2 --; R.sub.1 may denote a hydrogen atom, a halogen atom, a nitro group, a 1-pyrrolyl group, an acetamido group, an amino group or a dimethylamino group; R.sub.2 may denote a hydrogen atom or a nitro group; R.sub.3 and R.sub.4 may denote a hydrogen atom; R.sub.8a and R.sub.8b which are the same may denote a chlorine atom or a methoxy group; R.sub.9 may denote a hydrogen atom or an amino group; R may denote a methyl group; and X may denote a methanesulfonamido group, a 1-imidazolyl group or a nitro group or a salts thereof are useful as antiarrhythmic drugs.

  以下一般式（I）的新型胺衍生物：##STR1## 其中：A可以表示--(CH.sub.2)--O--, --(CH.sub.2).sub.2 --O--, 或--(CH.sub.2).sub.2 --NH--; B可以表示--(CH.sub.2).sub.2 --; R.sub.1可以表示氢原子、卤原子、硝基基团、1-吡咯基团、乙酰胺基团、氨基团或二甲胺基团; R.sub.2可以表示氢原子或硝基基团; R.sub.3和R.sub.4可以表示氢原子; R.sub.8a和R.sub.8b相同，可以表示氯原子或甲氧基团; R.sub.9可以表示氢原子或氨基团; R可以表示甲基基团; X可以表示甲磺酰氨基团、1-咪唑基团或硝基团或其盐，可用作抗心律失常药物。
• Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-<i>b</i>]benzoxazoles
  作者：Ke-Lai Li、Zong-Bo Du、Can-Cheng Guo、Qing-Yun Chen

  DOI：10.1021/jo900267c

  日期：2009.5.1

  o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for

  在已知的化合物2-（苯并恶唑-2'-基）-3-二甲基氨基丙烯醛中，邻乙酰氨基酚（2）与Vilsmeier试剂在Meth-Cohn条件下反应生成2-甲酰基吡啶并[2,1- b ]苯并恶唑（5） （4）。在乙酸酐中回流4得到4-甲酰基吡啶并[2,1- b ]苯并恶唑（6），其为5的异构体。两个图5a和6a中进行了结构表征通过X射线晶体学。5的形成机理 提出了包括顺序氯化，二聚化，分子内去除HCl形成恶唑环，两次甲酰化以及区域选择性分子内亲核环化以构建吡啶酮环的方法。
• Coupling compounds and hair dyeing compositions containing them
  申请人：DyStar Textilfarben GmbH & Co. Deutschland KG

  公开号：EP1847528A1

  公开（公告）日：2007-10-24

  The present invention refers to compounds of the formula (I) wherein R1 is (C1-C4)-alkyl, (C1-C4)-alkyl which is substituted by hydroxy, (C1-C4)-alkoxy, hydroxy-(C1-C4)-alkoxy, CN, -COOR5, -CON(R5)2 or -N(R5)2 or is phenyl; R2 is hydrogen, methyl or ethyl; R3 is (C1-C4)-alkylsulfonyl, (C1-C4)-alkylsulfonyl which is substituted by hydroxy, halogen, cyano, (C1-C4)-alkoxy or -N(R5)2 or is -SO2-CH=CH2, -SO2N(R5)2 or -PO(OR5)2; R4 is hydrogen, (C2-C4)-alkyl which is substituted by hydroxy, (C1-C4)-alkoxy or hydroxy-(C1-C4)-alkoxy; each of R5, independently is hydrogen, (C1-C4)-alkyl or hydroxy-(C2-C4)-alkyl; whereas R3 is not -NHSO2CH3 if R2 and R4 are both hydrogen and R1 is methyl, as well as hair dye compostions containing them.

  本发明涉及以下式(I)的化合物其中R1是(C1-C4)-烷基，被羟基取代的(C1-C4)-烷基，(C1-C4)-氧烷基，羟基-(C1-C4)-氧烷基，CN，-COOR5，-CON(R5)2或-N(R5)2或是苯基；R2是氢，甲基或乙基；R3是(C1-C4)-烷基磺酰基，被羟基，卤素，氰基，(C1-C4)-氧烷基或-N(R5)2取代的(C1-C4)-烷基磺酰基，或是-SO2-CH=CH2，-SO2N(R5)2或-PO(OR5)2；R4是氢，被羟基，(C1-C4)-氧烷基或羟基-(C1-C4)-氧烷基取代的(C2-C4)-烷基；R5中的每一个独立地是氢，(C1-C4)-烷基或羟基-(C2-C4)-烷基；其中如果R2和R4都是氢且R1是甲基，则R3不是-NHSO2CH3，以及含有它们的染发组合物。
• Oxidation dyeing compositions containing a cationic coupling agent, novel cationic coupling agents
  申请人：L'Oreal

  公开号：US06419711B1

  公开（公告）日：2002-07-16

  The invention concerns an oxidation dyeing composition for keratinous fibers containing at least a monobenzene coupling agent including at least a cationic group Z bearing at least a cyclized or non-cyclized quaternary ammonium unit, the use of said coupling agents for dyeing keratinous fibers, dyeing methods using same, and novel monobenzene coupling agents comprising at least a cationic group Z bearing at least a cyclized or non-cylized quaternary ammonium.

  这项发明涉及一种氧化染料组合物，用于染色角蛋白纤维，其中至少包含一种单苯偶联剂，包括至少带有至少一个环化或非环化的季铵单元的阳离子基团Z，使用该偶联剂来染色角蛋白纤维，使用相同的染色方法，以及包括至少带有至少一个环化或非环化季铵单元的阳离子基团Z的新型单苯偶联剂。