N-(4-羟基-3-硝基苯基)乙酰胺 | 51288-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: N-(4-羟基-3-硝基苯基)乙酰胺
• 英文名称: N-(4-hydroxy-3-nitrophenyl)acetamide
• 英文别名: 4-acetamino 2-nitro phenol；3-nitro-N-acetyl-p-aminophenol；4-hydroxy-3-nitroacetanilide；2-Nitro-4-acetamidophenol；4-hydroxy acetanilide；3-nitroacetaminophen
• CAS: 51288-37-0
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: XZYRROIQJHLVRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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

反应信息

• 作为反应物：
  描述：

  N-(4-羟基-3-硝基苯基)乙酰胺 在 盐酸 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 3.75h， 生成 4-hydroxy-3-nitrobenzenediazonium tetrafluoroborate
  参考文献：
  名称：

  阿卡巴霉素 G 的全合成，一种来自弧菌属的硝基苯基吲哚基马来酰亚胺海洋生物碱。世界工商管理硕士

  摘要：

  首次公开了海洋生物碱阿卡巴霉素 G 的全合成。合成顺序涉及逐步向马来酰亚胺中添加吲哚基序和衍生自对乙酰氨基酚的取代重氮苯系单元。还报道了使用受保护的苯酚的替代策略。

  DOI：

  10.1021/acs.joc.2c00063
• 作为产物：
  描述：

  2-硝基-4-氨基苯酚 在 乙酸酐 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 N-(4-羟基-3-硝基苯基)乙酰胺
  参考文献：
  名称：

  Pyrimidinedione compounds, method of producing the same and

  摘要：

  一种嘧啶二酮衍生物化合物具有一个基本的骨架，其中苯基部分和嘧啶二酮部分通过含有至少两个氮原子的烷基链连接。这种嘧啶二酮衍生物对治疗心律失常具有医疗用途。

  公开号：

  US05008267A1

文献信息

• METHOD FOR PRODUCING A CROSS-COUPLING PRODUCT OF A BENZENOID DIAZONIUM SALT
  申请人：Boege Nicolas

  公开号：US20130053598A1

  公开（公告）日：2013-02-28

  The invention relates to a method for producing a cross-coupling product of a benzenoid dizonium salt according to the general formula (I), wherein the groups R 1 , R 2 , R 3 , R 4 , and R 5 represent hydrogen, halogen, an alkyl, alkenyl, aryl, alkoxy, aryloxy, nitro, cyano, hydroxy, acetyl, and/or diazo groups independently of each, and X represents BF 4 , Cl, F, SO 3 CH 3 , CO 2 CH 3 , PF 6 , ClO 2 CH 3 , or CIO 4 , comprising the following steps: (a) providing a benzenoid amide, which with the exception of the diazo function has the same substituents R 1 , R 2 , R 3 , R 4 , and R 5 as the benzenoid diazonium salt of the general formula (I), and hydrolytically cleaving the amide to form an amine or providing a corresponding amine, (b) diazotizing the amine thus obtained or provided with a nitrite, and (c) subsequently reacting the benzenoid diazonium salt with a coupling partner in the presence of a catalyst to form a cross-coupling product, wherein the coupling parter is represented by the general formula (II), R 6 , R 7 , and R 8 are the same or different and represent hydrogen, carboxyalkyl groups, carboxyaryl groups, alkyl groups, aryl groups, alkoxy groups, aryloxy groups, wherein the groups can each contain Si, N, S, O, and or halogen atoms, or R 6 and R 7 with the double bound form an aromatic ring, which can be provided with R 8 and one to four further substituents, independently of each other, selected from the group comprising a straight-chain or branched (C 1 -C 6 ) alkyl group, a (C 3 -C 7 ) cycloalkyl group, a straight-chain or branched (C 1 -C 6 ) alkenyl group, a straight-chain or branched (C 1 -C 6 ) alkyoxy group, halogen, the hydroxy group, an amino, di(C 1 -C 6 ) alkylamino, nitro, acetyl, cyan, benzyl, 4-methoxybenzyl, 4-nitrobenzyl, phenyl, and 4-methoxyphenyl group and represents Y=H, —B(OR) 2 , —SnR 3 , —ZnR, —SiR 3 , or Mg (halogen), and wherein at least the steps (b) and (c) are performed without intermediate isolation of an intermediate product. According to said method, cross-couplings can be performed more simply and with improved yield without the hydroxyl group in aromatic reactants containing hydroxyl groups having to be provided with a protective group.

  该发明涉及一种根据通式(I)制备苯并重氮盐的交叉偶联产物的方法，其中基团R1、R2、R3、R4和R5代表氢、卤素、烷基、烯基、芳基、烷氧基、芳氧基、硝基、氰基、羟基、乙酰基和/或重氮基，X代表BF4、Cl、F、SO3CH3、CO2CH3、PF6、ClO2CH3或CIO4，包括以下步骤：(a)提供苯并酰胺，除了重氮功能外，具有通式(I)中苯并重氮盐相同的取代基R1、R2、R3、R4和R5，并水解裂解酰胺形成胺或提供相应的胺，(b)用亚硝酸盐重氮得到或提供的胺，(c)随后在催化剂存在下将苯并重氮盐与偶联配体反应形成交叉偶联产物，其中偶联配体由通式(II)表示，R6、R7和R8相同或不同，代表氢、羧基烷基、羧基芳基、烷基、芳基、烷氧基、芳氧基，其中基团可以包含Si、N、S、O和/或卤素原子，或R6和R7与双键形成芳香环，可提供R8和一个到四个进一步取代基，独立于彼此，选自包括直链或支链(C1-C6)烷基、(C3-C7)环烷基、直链或支链(C1-C6)烯基、直链或支链(C1-C6)烷氧基、卤素、羟基、氨基、二(C1-C6)烷基氨基、硝基、乙酰基、氰基、苄基、4-甲氧基苄基、4-硝基苄基、苯基和4-甲氧基苯基，表示Y=H、—B(OR)2、—SnR3、—ZnR、—SiR3或Mg(卤素)，至少步骤(b)和(c)在不中间分离中间产物的情况下执行。根据该方法，可以更简单地进行交叉偶联，并且在含有羟基的芳香反应物中无需提供保护基即可获得改进的产率。
• A Deacetylation-Diazotation-Coupling Sequence: Palladium- Catalyzed CC Bond Formation with Acetanilides as Formal Leaving Groups
  作者：Bernd Schmidt、René Berger

  DOI：10.1002/adsc.201200929

  日期：2013.2.1

  Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki cross-coupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition have been investigated as terminating CC bond-forming steps of this one-flask sequence. The sequence does not require the exchange of solvents or removal

  乙酰苯胺可以原位脱乙酰化和重氮化，然后在不分离重氮中间体的情况下用于Pd催化的偶联反应中。Heck反应，Suzuki交叉偶联反应和Pd催化的[2 + 2 + 1]环加成反应已作为该一瓶序列的终止CC键形成步骤进行了研究。该顺序不需要在各个步骤之间交换溶剂或除去副产物，而是在适当的时候通过添加试剂和催化剂来进行。
• PEG-N₂O₄: An Efficient Nitrating Agent for the Selective Mono- and Dinitration of Phenols Under Mild Conditions
  作者：Mohammad Ali Zolfigol、Elaheh Madrakian、Ezat Ghaemi、Khodabakhsh Niknam

  DOI：10.1080/00397910802136706

  日期：2008.9.12

  was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N2O4 (PEG-N2O4) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N2O4 at room temperature in moderate to high yields.

  摘要 N2O4 很容易浸渍在聚乙二醇上，得到稳定的试剂。聚乙二醇-N2O4（PEG-N2O4）体系被用作苯酚硝化的有效硝化剂。单硝基苯酚和二硝基苯酚可以通过苯酚在 PEG-N2O4 存在下在室温下以中等至高产率直接硝化获得。
• A practical approach for regioselective mono-nitration of phenols under mild conditions
  作者：Ling-Yan Chen、Tao Liu、Xiaokun Zhou、Zhihua Sun

  DOI：10.3998/ark.5550190.p008.587

  日期：——

  Cu(NO 3)2.3H 2O was demonstrated to be an efficient, regioselect ive and inexpensive nitrating reagent for the synthesis of mono-nitro substituted phenolic compounds. 12 examples of different phenols were examined. Good yields (67-90%) have been achieved.

  Cu(NO 3)2.3H 2O 被证明是一种高效、区域选择性和廉价的硝化试剂，用于合成单硝基取代的酚类化合物。检查了 12 个不同酚类的例子。已经实现了良好的产率 (67-90%)。
• Mizoroki-Heck Reactions with 4-Phenoldiazonium Salts
  作者：Bernd Schmidt、Frank Hölter、René Berger、Sönke Jessel

  DOI：10.1002/adsc.201000493

  日期：2010.10.4

  Significantly better yields were achieved in Mizoroki–Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation–diazotation–precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these

  在其他条件相同的条件下，使用4-苯酚重氮盐代替O-烷基化类似物，在Mizoroki-Heck反应中获得了明显更高的收率。我们发现，从扑热息痛或扑热息痛衍生的对乙酰苯胺开始的一烧瓶式脱乙酰化-重氮化反应-沉淀序列为获得所需的重氮四氟硼酸盐提供了便利。这些芳基化剂在钯催化的CC键形成反应中的实用性已被证明可用于一瓶合成药物阿立哌唑的杂环核心。值得注意的是，由乙苯胺形成的重氮盐可与两个Pd催化的步骤以一个烧瓶的顺序合并，而无需任何溶剂交换或中间体分离。