3-硝基-4-乙酰氨基苯酚 | 7403-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-硝基-4-乙酰氨基苯酚
• 英文名称: N-(4-hydroxy-2-nitrophenyl)-acetamide
• 英文别名: 1-acetamido-4-hydroxy-2-nitrobenzene；N-(4-hydroxy-2-nitrophenyl)acetamide；4-hydroxy-2-nitroacetanilide；4-acetamido-3-nitro-phenol；3-nitro-4-acetamidophenol；3-nitro 4-acetylamino phenol
• CAS: 7403-75-0
• 化学式: C₈H₈N₂O₄
• 分子量: 196.163
• InChiKey: OZZKMZSOGAOIFX-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220°C
• 沸点：
  459.1±40.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：

  3-硝基-4-乙酰氨基苯酚 在 sodium carbonate 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-{4-[5-(4-chlorophenoxy)pentyloxy]-2-nitrophenyl}acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063
• 作为产物：
  描述：

  对乙酰氨基酚 在 dipotassium peroxodisulfate 、 silver(I) nitrite 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以67%的产率得到3-硝基-4-乙酰氨基苯酚
  参考文献：
  名称：

  银催化的苯胺的化学和区域选择性硝化

  摘要：

  通过C–H键官能化对苯甲酰胺进行高度区域选择性的银催化硝化可产生相应的邻硝基硝基苯胺，产率中等至良好。反应以NaNO 2作为硝化剂进行。

  DOI：

  10.1002/ejoc.201800779

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。
• 7(8)-Substituted triazinobenzimidazoles and anthelmintic compositions
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04011320A1

  公开（公告）日：1977-03-08

  7(8)-substituted triazinobenzimidazoles represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R' is diloweralkylaminoalkyl (C.sub.2-6) or alkyl having 1 to 18 carbon atoms; R.sup.2 is phenylsulfinyl, phenoxyethoxy, benzyloxyethoxy, methoxyethylsulfinyl, or 3-chloroprop-1-ylsulfinyl; the R.sup.2 -substitution being at the 7(8)-position; or a pharmaceutically acceptable salt thereof. The compounds are useful as pesticides, particularly as antifungal and anthelmintic agents.

  7(8)-取代的三嗪苯并咪唑的化合物由以下公式表示：##STR1##其中R是具有1至4个碳原子的低碳基团；R'是二低碳氨基烷基（C.sub.2-6）或具有1至18个碳原子的烷基；R.sup.2是苯基亚砜基、苯氧乙氧基、苄氧乙氧基、甲氧基乙基亚砜基或3-氯丙-1-基亚砜基；R.sup.2-取代位于7(8)-位置；或其药学上可接受的盐。这些化合物可用作杀虫剂，特别是作为抗真菌和抗蠕虫剂。
• 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04072696A1

  公开（公告）日：1978-02-07

  Carbalkoxythioureidobenzene derivatives represented by the following formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is --SR.sup.2, --SOR.sup.2, --SO.sub.2 R.sup.2, --OR.sup.2, --SCN, --SC(O)NR.sup.3 R.sup.4, or --M'(CH.sub.2).sub.n MR.sup.7 where n is 1-4; R.sup.2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, aralkyl or aryl, provided that when R.sup.1 is --SO.sub.2 R.sup.2, R.sup.2 is not aralkyl or phenyl; R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; Y is amino, nitro, acylamino where the acyl portion has 1 to 6 carbon atoms, --NHC(O) (CH.sub.2).sub.m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR2## and R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl. The R.sup.1 substitution is either at the 4- or 5-position. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.

  以下是该公式代表的Carbalkoxythioureidobenzene衍生物的中文翻译：其中R是具有1至4个碳原子的低碳基团；R.sup.1是--SR.sup.2，--SOR.sup.2，--SO.sub.2 R.sup.2，--OR.sup.2，--SCN，--SC(O)NR.sup.3 R.sup.4，或--M'(CH.sub.2).sub.n MR.sup.7，其中n为1-4；R.sup.2是具有1至6个碳原子的低碳基，具有3至7个碳原子的环烷基，具有3至6个碳原子的低烯基或低炔基，芳基烷基或芳基，但当R.sup.1为--SO.sub.2 R.sup.2时，R.sup.2不是芳基烷基或苯基；R.sup.3和R.sup.4独立地是氢或具有1至6个碳原子的低碳基；Y是氨基，硝基，酰胺基，其中酰基部分具有1至6个碳原子，--NHC(O) (CH.sub.2).sub.m COOH，其中m为1-6，或--NHC(S)NHCOOR；M和M'独立地是O，S或##STR2##，R.sup.7是具有1至4个碳原子的低碳基或芳基。R.sup.1取代物位于4-或5-位置。这些化合物可用作杀虫剂，特别是作为驱虫剂和抗真菌剂。
• Compounds which can be used for hair dyeing, process for their
  申请人：L'Oreal

  公开号：US04888025A1

  公开（公告）日：1989-12-19

  The present invention relates to new 1-(substituted phenoxy)-3-aminopropan-2-ol compounds in which the extra-nuclear amine group may or may not be substituted, and to the process for their preparation. The invention also relates to hair-dyeing compositions containing these new compounds and to a dyeing process using the said compositions.

  本发明涉及新的1-(取代苯氧基)-3-氨基丙-2-醇化合物，其中额外的非核胺基团可能被取代，也可能不被取代，以及它们的制备过程。该发明还涉及含有这些新化合物的染发剂组合物以及使用所述组合物的染发过程。
• 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。