N-(4-溴苯基)-4-硝基苯甲酰胺 | 59280-03-4

• 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-(4-溴苯基)-4-硝基苯甲酰胺
• 中文别名: N-(4-溴苯)-4-硝基苯甲酰胺,97
• 英文名称: N-(4-bromophenyl)-4-nitrobenzamide
• CAS: 59280-03-4
• 化学式: C₁₃H₉BrN₂O₃
• mdl: MFCD00438175
• 分子量: 321.13
• InChiKey: WXCIUWMZYPAPDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  247 °C
• 沸点：
  381.4±27.0 °C(Predicted)
• 密度：
  1.635±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(4-溴苯基)-4-硝基苯甲酰胺 在 劳森试剂 、 sodium hydroxide 、 乙醇 、 potassium carbonate 、 tin(ll) chloride 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 二甲基亚砜 、 氯苯 为溶剂， 反应 24.0h， 生成 2-(4-methylaminophenyl)-6-bromobenzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹¹C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents

  摘要：

  The synthesis and evaluation of a series of neutral analogues of thioflavin-T (termed BTA's) with high affinities for aggregated amyloid and a wide range of lipophilicities are reported. Radiolabeling with high specific activity [C-11]methyl iodide provided derivatives for in vivo evaluation. Brain entry in control mice and baboons was high for nearly all of the analogues at early times after injection, but the clearance rate of radioactivity from brain tissue varied by more than 1 order of magnitude. Upon the basis of its rapid clearance from normal mouse and baboon brain tissues, [N-methyl-C-11]2-(4'-methylaminophenyl)-6-hydroxybenzothiazole (or [C-11]6-OH-BTA-1) was selected as the lead compound for further evaluation. The radiolabeled metabolites of [C-11]6-OH-BTA-1 were polar and did not enter brain. The binding affinities of [N-methyl-H-3]6-OH-BTA-1 for homogenates of postmortem AD frontal cortex and synthetic Abeta(1-40) fibrils, were similar (K-d = 1.4 nM and 4.7 nM, respectively), but the ligand-to-Abeta peptide binding stoichiometry was similar to400-fold higher for AD brain than Abeta(1-40) fibrils. Staining of AD frontal cortex tissue sections with 6-OH-BTA-1 indicated the selective binding of the compound to amyloid plaques and cerebrovascular amyloid. The encouraging in vitro and in vivo properties of [C-11]6-OH-BTA-1 support the choice of this derivative for further evaluation in human subject studies of brain Abeta deposition.

  DOI：

  10.1021/jm030026b
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 4-溴苯胺 以 二氯甲烷 为溶剂， 反应 0.25h， 以72%的产率得到N-(4-溴苯基)-4-硝基苯甲酰胺
  参考文献：
  名称：

  使用硅烷/氧-R配合物体系高度还原芳香硝基化合物的化学和区域选择性

  摘要：

  据报道，由高价氧-hen络合物催化的硅烷将芳族硝基化合物还原为相应的胺。PhMe 2 SiH / ReIO 2（PPh 3）2（5 mol％）和PhMe 2 SiH / ReOCl 3（PPh 3）2（5 mol％）催化体系在宽范围的存在下有效还原了一系列芳族硝基化合物官能团的范围，例如酯，卤素，酰胺，砜，内酯和苄基。该方法还允许在脂肪族硝基存在下将二硝基苯区域选择性还原成相应的硝基苯胺和将芳族硝基还原。

  DOI：

  10.1021/jo9008657

文献信息

• Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon
  作者：Jian-Quan Liu、Xuanyu Shen、Zhenhua Liu、Xiang-Shan Wang

  DOI：10.1039/c7ob01449j

  日期：——

  An interesting radical coupling reaction of aromatic aldehydes with isocyanides was disclosed for the synthesis of amides catalyzed by copper. According to the experimental results and mechanistic study, the isocyano group acted as an N1 synthon rather than exhibiting the carbene-like reactivity, exploiting a new reactivity profile of isocyanides.

  公开了一种有趣的芳族醛与异氰酸酯的自由基偶联反应，用于合成铜催化的酰胺的合成。根据实验结果和机理研究，异氰酸酯基团起N1合成子的作用，而不是表现出卡宾样的反应性，从而利用了异氰酸酯的新反应性特征。
• Imidazolium salt-supported Mukaiyama reagent: an efficient condensation reagent for amide bond formation
  作者：Khima Pandey、Manoj Kumar Muthyala、Sunita Choudhary、Anil Kumar

  DOI：10.1039/c4ra14856h

  日期：——

  A novel imidazolium salt-supported Mukaiyama reagent (2-chloropyridinium salt) has been developed and explored as an efficient coupling agent for amide bond formation. The use of an ionic liquid-supported reagent enabled isolation of the amide products by simple extraction with organic solvents in high purity and avoiding column chromatography purification.

  已经开发了新型咪唑鎓盐负载的Mukaiyama试剂（2-氯吡啶鎓盐），并将其作为形成酰胺键的有效偶联剂进行了探索。通过使用离子液体负载的试剂，可以通过简单地以高纯度用有机溶剂萃取并避免柱色谱纯化来分离酰胺产物。
• Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights
  作者：Girish Bolakatti、Mahesh Palkar、Manjunatha Katagi、Girish Hampannavar、Rajshekhar V. Karpoormath、Shilpa Ninganagouda、Arvind Badiger

  DOI：10.1016/j.molstruc.2020.129413

  日期：2021.3

  Abstract A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures

  摘要 3-(2-(4-(取代-苯并[d]噻唑-2-基)苯基氨基)乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-酮(7a -f 和 8a-f) 合成。适当取代的 2-(4-氨基苯基)苯并[d]噻唑 (4a-f) 与 3-(2-溴乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-one 的反应 ( 5/6) 在冰醋酸的存在下产生所需的化合物。合成化合物的结构基于它们的光谱（IR、1H NMR、13C NMR和MS）和元素分析来表征。细胞毒性筛选研究表明，MCF-7 和 WRL68 癌细胞对所有测试化合物均敏感。在 12 种新型杂交体中，化合物 8f 显示出最显着的抗癌活性。进行对接研究以了解标题化合物在目标酶（EGFR 酪氨酸激酶，1M17）活性位点的结合模式。化合物 8f 和 7f 显示出针对 1M17 的显着且保守的结合相互作用。此外，化合物 7e、7f、8e 和 8f 表现出有趣
• A Comparison of Immobilised Triphenylphosphine and 1‐Hydroxybenzotriazole as Mediators of Catch‐and‐Release Acylation Under Flow Conditions
  作者：Joseph Tadros、Christian Dankers、Ashley Jurisinec、Maria Menti‐Platten、Janice R. Aldrich‐Wright、Christopher P. Gordon

  DOI：10.1002/asia.202101308

  日期：2022.3

  A ‘catch-and-release’ assessment of immobilised triphenylphosphine (PS-PPh3) and 1-hydroxybenzotriazole (PS-HOBt) as facilitators of acylation-mediated amide couplings is described. Through evaluations of reaction temperatures, substrate stoichiometries, solvents, and flow rates, we report findings in favour of PS-HOBt over PS-PPh3.

  描述了作为酰化介导的酰胺偶联促进剂的固定化三苯膦 (PS-PPh 3 ) 和 1-羟基苯并三唑 (PS-HOBt)的“捕获和释放”评估。通过对反应温度、底物化学计量、溶剂和流速的评估，我们报告了有利于 PS-HOBt 优于 PS-PPh 3的发现。
• Kinetics and mechanism of the aminolysis of benzoic anhydrides
  作者：Byung Choon Lee、Ji Hyun Yoon、Cheal Gyu Lee、Ikchoon Lee

  DOI：10.1002/poc.610070602

  日期：1994.6

  the latter, indicate that the reaction proceeds by a frontside SN2 attack on either one of the caronyl carbon with a strong interaction between the nucleophile (X) and the leaving group (Z). The mechanism is also supposed by the trends in the activation parameters.

  在甲醇中研究了苯环被苯环取代的苯甲酸酐的亲核取代反应。产物形成步骤与限速步骤一致，因此可以分解竞争反应途径的两个速率常数k XZ和k XZ。两个交叉相互作用常数，ρ XY和ρ XY，尤其是一个异常大的幅度后者的，表明该反应的进行通过前侧小号Ñ 2攻击的caronyl碳与亲核试剂之间的强烈的相互作用的任一个（X ）和离去组（Z）。激活参数的趋势也可以推测这种机制。