4-甲氧基-N-(2-硝基苯基)苯甲酰胺 | 7464-50-8

• 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: 4-甲氧基-N-(2-硝基苯基)苯甲酰胺
• 英文名称: 4-methoxy-N-(2-nitrophenyl)benzamide
• CAS: 7464-50-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: RZIZNTUSSFMRTC-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  367.2±27.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基-N-(2-硝基苯基)苯甲酰胺 在 氢气 、 钯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 生成 2-{2-[(4-methoxybenzoyl)amino]anilino}-2-oxoethylacetate
  参考文献：
  名称：

  A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds

  摘要：

  A series of dithiobenzanilide derivatives was synthesized and each compound was evaluated for its ability to reduce KCl-induced contractions of smooth muscle preparations of the guinea pig. Starting from a recent publication describing benzanilide derivatives as antispasmodic agents, structure-activity guided synthesis was performed to obtain compounds with improved spasmolytic activity. First, compounds with two amide bonds were designed and second, both amide oxygens were replaced by two sp(2) sulfur atoms resulting in dithiobenzanilide derivatives. The most potent antispasmodic dithiobenzanilide 19 showed improved activity with an IC50 value of 0.4 mu M. Moreover, the study also demonstrated that these active compounds were able to antagonize the effect of spasmogens like acetylcholine and phenylephrine and that the activity is not mediated by activation of ATP-dependent potassium channels (K-ATP-channels) or inhibition of endothelial nitric oxide synthase (eNOS). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.043
• 作为产物：
  描述：

  大茴香酸 在 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 25.5h， 生成 4-甲氧基-N-(2-硝基苯基)苯甲酰胺
  参考文献：
  名称：

  Oligoamide Foldamers家族中的折叠模式

  摘要：

  合成了一系列小的，不对称的吡啶-2,6-二羧基酰胺低聚酰胺折叠剂，它们在末端基团上具有不同的长度和取代基，以研究其构象性质和折叠模式。@型折叠模式类似于酶的氧阴离子孔基序，但也可以表征几种其他的折叠模式。计算研究表明，稳定性几乎相等的几种替代构象异构体。这些折叠模式在分子内氢键模式和芳基-芳基相互作用方面互不相同。在固态状态下，折叠器采用球状@型折叠或扩展的S型构象，这与通过计算获得的折叠器非常相似。在某些情况下，相同的折叠分子甚至可以结晶成两种不同的折叠模式，从而证实尽管形状完全不同，但不同的折叠模式在能量上却非常接近。最后，在液态下观察到的NOE相互作用的最佳匹配是一个构象，该构象与计算得出的螺旋型折叠相匹配。

  DOI：

  10.1002/chem.201406521

文献信息

• Antithrombotic agents
  申请人：Eli Lilly and Company

  公开号：US06417200B1

  公开（公告）日：2002-07-09

  This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  这种应用涉及到式(I)的化合物，该化合物的药用盐或其前药，如本文所定义的，以及其药物组合物，以及其作为Xa因子抑制剂的用途，以及其制备方法和中间体。
• Copper-Catalyzed Direct Nitration on Aryl C–H Bonds by Concomitant Azidation–Oxidation with TMS Azide and TBHP under Aerobic Conditions
  作者：Botla Vinayak、Malapaka Chandrasekharam

  DOI：10.1021/acs.orglett.7b01489

  日期：2017.7.7

  An unprecedented copper-catalyzed in situ azidation–oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr–H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.

  通过直接的C Ar -H功能化，开发出了前所未有的铜催化原位叠氮化氧化技术，用于苯胺和磺酰胺的硝化。使用TMSN 3和TBHP可以实现这种新颖而高效的硝化方案，而不会排除空气或湿气。已经研究了2-硝基苯胺的合成应用。
• Effective Nitration of Anilides and Acrylamides by<i>tert</i>-Butyl Nitrite
  作者：Yi-fei Ji、Hong Yan、Qi-bai Jiang

  DOI：10.1002/ejoc.201403510

  日期：2015.3

  [10% Cu(NO3)(2)3H(2)O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array

  硝基化合物是合成有机化学和化学工业中的重要中间体。在此，以TBN（亚硝酸叔丁酯）为硝化试剂，开发了铜催化[10% Cu(NO3)(2)3H(2)O]硝化苯胺的高效硝化反应，得到相应的硝基取代芳烃产物。良好的产量。TBN 的使用还导致丙烯酰胺在室温下选择性硝化以仅提供硝化产物的 (E) 异构体。该程序对一系列具有广泛官能团的苯胺和丙烯酰胺具有良好的耐受性。该合成方法具有原料廉价、反应条件温和、反应速度快、收率高等优点。机理研究表明，一个硝基自由基，
• Route to pyrrolo[1,2-a]quinoxalines via a furan ring opening-pyrrole ring closure sequence
  作者：Elena Y. Zelina、Tatyana A. Nevolina、Ludmila N. Sorotskaja、Dmitry A. Skvortsov、Igor V. Trushkov、Maxim G. Uchuskin

  DOI：10.1016/j.tetlet.2019.151532

  日期：2020.2

  A method was developed for the synthesis of pyrrolo[1,2-a]quinoxalines based on an acid-promoted furan ring opening of readily accessible N-(furan-2-ylmethyl)-2-nitroanilines or their heterocyclic analogues followed by a key reductive Paal-Knorr cyclization of the corresponding nitro-1,4-diketones.

  基于容易获得的N-（呋喃-2-基甲基）-2-硝基苯胺或其杂环类似物随后加关键的酸促进的呋喃开环，开发了一种合成吡咯并[1,2-a]喹喔啉的方法相应的硝基-1,4-二酮的还原性Paal-Knorr环化反应。
• CuSO4-mediated decarboxylative C–N cross-coupling of aromatic carboxylic acids with amides and anilines
  作者：Wei-Jian Sheng、Qing Ye、Wu-Bin Yu、Ren-Rong Liu、Meng Xu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1016/j.tetlet.2014.12.085

  日期：2015.1

  CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently with aromatic carboxylic acids to give diarylamines in good to excellent yields. (C) 2014 Published by Elsevier Ltd.