N-(2-羟基苯基)-4-硝基苯甲酰胺 | 3743-17-7

• 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: N-(2-羟基苯基)-4-硝基苯甲酰胺
• 英文名称: N-(2-hydroxy-phenyl)-4-nitro-benzamide
• 英文别名: N-(2-hydroxyphenyl)-4-nitrobenzamide；N-(p-nitrobenzoyl)-o-aminophenol；4-nitro-benzoic acid-(2-hydroxy-anilide)；4-Nitro-benzoesaeure-(2-hydroxy-anilid)；N-o-Hydroxyphenyl-p-nitrobenzamid
• CAS: 3743-17-7
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: XZBRJALGZPKRBK-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  369.9±27.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)
• 溶解度：
  24.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(2-羟基苯基)-4-硝基苯甲酰胺 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 23.0h， 以28%的产率得到2-(4-硝基苯基)-苯并噁唑
  参考文献：
  名称：

  以PPh3-DDQ为脱水剂方便合成2-恶唑啉和2-苯并恶唑

  摘要：

  用三苯基膦-2,3-二氯-5,6-二氰基苯并醌（PPh 3 -DDQ）作为脱水和活化试剂分别从酰基氨基醇和酰基氨基苯酚分别以高收率合成了2-恶唑啉和2-苯并恶唑。该合成在中性条件下完成。

  DOI：

  10.1002/cjoc.201190190
• 作为产物：
  描述：

  对硝基苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醚 、 水 、 苯 为溶剂， 反应 3.0h， 生成 N-(2-羟基苯基)-4-硝基苯甲酰胺
  参考文献：
  名称：

  Synthesis and microbiological activity of some N-(o-hydroxyphenyl)benzamides and phenylacetamides as the possible metabolites of antimicrobial active benzoxazoles: part II

  摘要：

  The synthesis of some N-(o-hydroxyphenyl)benzamides and benzacetamides (2a-2p) in order to determine their in vitro antimicrobial activity against two Gram-positive bacteria, three Gram-negative bacteria and the fungus Candida albicans is described. The new compounds were compared with several control drugs. The derivative 2g, 4-amino-N-(o-hydroxyphenyl)benzamide, was found active at an MIC value of 25 mug/ml against the Gram-negative microorganism Klebsiella pneumoniae. Most of the compounds exhibited antibacterial activity at an MIC value of 25 mug/ml against Pseudomonas aureginosa. For the antifungal activity against C. albicans, compounds 2e, 2h and 2m were found more active than the other derivatives (MIC 12.5 mug/ml). The antimicrobial activity of some of these benzamide and phenylacetamide derivatives (2a, 2b, 2f, 2g, 2h and 2k), possible metabolites of benzoxazoles, was also compared with that of the cyclic analogues 3-8. Compound 2f possesses two dilutions better antifungal activity than its cyclic analogue the benzoxazole derivative 5 against C. albicans, while having one dilution better antibacterial activity against Streptococcus faecalis and K. pneumoniae. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00070-7

文献信息

• Iron(III) Chloride Mediated <i>para</i> ‐Selective C‐H Functionalization: Access to C5‐Chloro and C5,C7‐Dichloro/Dianisyl Substituted 2‐Arylbenzoxazoles
  作者：Kanchanbala Sahoo、Niranjan Panda

  DOI：10.1002/adsc.202101359

  日期：2022.3

  Iron(III) chloride mediated para-selective C−H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole by ferric chloride was explored to achieve the remotely anisylated benzoxazoles.

  开发了氯化铁 (III) 介导的对位选择性 C-H 氯化和随后的 2-氨基苯酚环化以合成 C5-和 C5、C7-氯化苯并恶唑。此外，还探索了三氯化铁对氨基苯酚与苯甲醚的氧化交叉脱氢偶联，以实现远程苯甲酰化苯并恶唑。
• Tertiary Amine-Catalyzed Acyl Group Exchange Reaction of<i>N</i>,<i>O</i>-Diacyl-<i>o</i>-aminophenols. Its Mechanism and Factors Determining the Relative Stability of Acyl Exchanged Isomer Pairs
  作者：Tadamitsu Sakurai、Shuichi Kojima、Hiroyasu Inoue

  DOI：10.1246/bcsj.63.3141

  日期：1990.11

  polarities. It was found that the relative stability of acyl exchanged isomer pairs is determined solely by the inductive effect of acyl groups, provided that the steric hindrance of acyl substituents bonded to amide nitrogen affects the stability to the same extent. The importance of steric hindrance exerted by a bulky acyl group in determining the relative stability was demonstrated by analyzing the

  已经在不同极性的溶剂中研究了酰基取代基对各种 N,O-二酰基-o-氨基苯酚的酰基交换反应的平衡和速率常数的影响。发现酰基交换的异构体对的相对稳定性仅由酰基的诱导作用决定，条件是与酰胺氮键合的酰基取代基的空间位阻对稳定性产生相同程度的影响。通过分析标准自由能变化 (ΔG°) 和 pKa 之间的相关性，证明了由庞大的酰基施加的空间位阻在确定相对稳定性方面的重要性，标准自由能变化 (ΔG°) 和 pKa 用作异构体对的相对稳定性的量度和分别为酰基的吸电子能力。另一方面，酰基迁移反应的催化速率常数的对数与 pKa 值密切相关。除了这个发现之外，激活熵的大负值 ΔS\eweq=...
• Tertiary Amine-Catalyzed Acyl Group-Exchange Reactions of<i>N</i>,<i>O</i>-Diacyl-<i>o</i>-aminophenols
  作者：Tadamitsu Sakurai、Shuichi Yamada、Hiroyasu Inoue

  DOI：10.1246/bcsj.59.2666

  日期：1986.8

  A kinetic study on the base-catalyzed acyl group-exchange reactions of N,O-diacyl-o-aminophenols was undertaken to show that the formation of the amidate ion should be the rate-determining step in these intramolecular acyl-exchange reactions, and that the electron-withdrawing power of acyl group becomes an important factor to control the relative stabilities of a pair of N,O-diacyl-o-aminophenols.

  对N,O-二酰基-o-氨基酚的碱催化酰基交换反应进行了动力学研究，表明在这些分子内酰基交换反应中，酰胺离子的形成应是速率决定步骤，并且酰基的电子吸引能力成为影响一对N,O-二酰基-o-氨基酚相对稳定性的一个重要因素。
• Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization
  作者：Christian Dankers、Joseph Tadros、David G. Harman、Janice R. Aldrich-Wright、Thanh V. Nguyen、Christopher P. Gordon

  DOI：10.1021/acscombsci.0c00001

  日期：2020.5.11

  injecting a single solution (1:9 dimethylformamide: dichloromethane) containing a carboxylic acid and an amine or linear peptide sequence into a continuous stream of dichloromethane. The protocol remained viable in the absence of base, did not require carboxylate preactivation which, and in concert with minimal workup requirements, enabled the isolation of products in high yields. Compared to the utilization

  通过在存在，不存在二异丙胺和苯并三唑添加剂的情况下或将其组合使用时，对反应温度，溶剂，碳二亚胺树脂和碳二亚胺摩尔当量的一百三十多种排列进行筛选，一种便捷且首次报道的碳二亚胺聚合物辅助流动方法开发了酰胺偶联和内酰胺化作用。该方案需要将包含羧酸和胺或线性肽序列的单一溶液（1：9二甲基甲酰胺：二氯甲烷）注入连续的二氯甲烷流中。该方案在没有碱的情况下仍然可行，不需要羧酸盐预活化，这与最低限度的后处理要求相结合，能够以高收率分离出产物。与使用非限制碳二亚胺试剂相比，
• Access to C4-arylated benzoxazoles from 2-amidophenol through C–H activation
  作者：Kanchanbala Sahoo、Priyanka Pradhan、Niranjan Panda

  DOI：10.1039/d0ob00061b

  日期：——

  A Pd-catalyzed aerobic approach to access C4-aryl benzoxazoles by tandem C-H ortho-arylation and acid-mediated annulation of 2-amidophenol has been presented. The directing potential of the -NHCOR group over the -OH group was exploited for selective arylation adjacent to the amide group. Deuterium labeling experiments suggest that palladation predominantly occurs adjacent to the -NHCOR group and is

  提出了一种通过Pd催化的好氧方法，通过串联CH邻位芳基化和酸介导的2-酰胺基苯酚来获得C4-芳基苯并恶唑。利用-NHCOR基团相对于-OH基团的定向电位来进行与酰胺基团相邻的选择性芳基化。氘标记实验表明，触诊主要发生在-NHCOR基团附近，并且是苯并恶唑形成过程中的关键步骤。还完成了所得到的C4-芳基化苯并恶唑的一锅水解，以获取结构上具有挑战性的3-芳基氨基苯酚以用于进一步的应用。