N-(4-氯苯基)-4-甲基苯甲酰胺 | 33667-89-9

• 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-氯苯基)-4-甲基苯甲酰胺
• 英文名称: N-(4-chlorophenyl)-4-methylbenzamide
• CAS: 33667-89-9
• 化学式: C₁₄H₁₂ClNO
• 分子量: 245.708
• InChiKey: WQWILBQLOABMSN-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C(Solv: ethanol (64-17-5))
• 沸点：
  305.7±35.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(4-氯苯基)-4-甲基苯甲酰胺 在 4-硝基碘苯 、 Oxone 、 三氟甲磺酸 作用下， 反应 12.0h， 以82%的产率得到6-chloro-2-(p-tolyl)benzo[d]oxazole
  参考文献：
  名称：

  Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C–H Functionalization and C–O/S Bond Formation

  摘要：

  An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

  DOI：

  10.1021/jo501216h
• 作为产物：
  描述：

  对甲基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(4-氯苯基)-4-甲基苯甲酰胺
  参考文献：
  名称：

  多取代的1,2,4-三唑的合成

  摘要：

  使用取代的亚氨基衍生物合成了一系列新的取代的1,2,4-三唑衍生物。 异烟碱基肼（或以4-硝基苯甲酰肼为主要中间体。这些化合物在1,2,4-三唑衍生物上包括不同的供体或受体取代基。这些化合物的结构通过FTIR，1 H-NMR，13 C-NMR和元素分析确认。

  DOI：

  10.1002/jhet.1031

文献信息

• One-pot synthesis of polyfunctionalized quinolines <i>via</i> a copper-catalyzed tandem cyclization
  作者：Dianpeng Chen、Xuejun Sun、Yingying Shan、Jinmao You

  DOI：10.1039/c8ob02078g

  日期：——

  An efficient one-pot approach for the synthesis of polyfunctionalized quinolines was developed via a sequence of copper-catalyzed coupling reaction/propargyl-allenyl isomerization/aza-electrocyclization. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.

  通过一系列的铜催化偶联反应/炔丙基-烯基异构化/氮杂-电环化，开发了一种高效的一锅法合成多官能喹啉。容易获得的起始原料，温和的条件以及广泛的底物范围使该方法具有潜在的实用性。
• Mn(III)-mediated radical cascade reaction of boronic acids with isocyanides: Synthesis of diimide derivatives
  作者：Fei Wang、Tian-Qi Wei、Pei Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.cclet.2018.08.006

  日期：2019.2

  Abstract A manganese(III)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acetyl diimide derivatives. New C C, C N and C O bonds were formed in one step.

  摘要研究了锰（Ⅲ）促进的易接近的芳基硼酸与异氰酸酯的氧化自由基级联反应，以构建二酰亚胺衍生物。该方案提供了一种合成乙酰二酰亚胺衍生物的新方法。一步就形成了新的CC，CN和CO键。
• Highly efficient synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones via Lewis acid assisted cyclization reaction
  作者：Kunyong Yang、Xiaohui He、Ha-soon Choi、Zhicheng Wang、David H. Woodmansee、Hong Liu

  DOI：10.1016/j.tetlet.2008.01.071

  日期：2008.3

  An expedient one-pot synthesis of fused bicyclic 2,3-diaryl-pyrimidin-4(3H)-ones from three readily available components is described. The key step is a Lewis acid assisted cyclization reaction.

  描述了一种方便的一锅合成法，它由三种容易获得的组分合成稠合的双环2，3-二芳基-嘧啶-4（3 H）-。关键步骤是路易斯酸辅助环化反应。
• Synthesis of Secondary Amides through the Palladium(II)-Catalyzed Aminocarbonylation of Arylboronic Acids with Amines or Hydrazines and Carbon Monoxide
  作者：Jin Zhang、Yuqiang Ma、Yangmin Ma

  DOI：10.1002/ejoc.201701802

  日期：2018.4.17

  A new Pd‐catalyzed aminocarbonylation of arylboronic acids with amines or hydrazines produces secondary amides. The method exhibits good atom‐economy and a wide functional group tolerance.

  芳族硼酸与胺或肼的新Pd催化氨基羰基化反应会生成仲酰胺。该方法具有良好的原子经济性和宽泛的官能团耐受性。
• Studies towards the Design and Synthesis of Novel 1,5-Diaryl-1H-imidazole-4-carboxylic Acids and 1,5-Diaryl-1H-imidazole-4-carbohydrazides as Host LEDGF/p75 and HIV-1 Integrase Interaction Inhibitors
  作者：Thompho J. Rashamuse、Muhammad Q. Fish、E. Mabel Coyanis、Moira L. Bode

  DOI：10.3390/molecules26206203

  日期：——

  Two targeted sets of novel 1,5-diaryl-1H-imidazole-4-carboxylic acids 10 and carbohydrazides 11 were designed and synthesized from their corresponding ester intermediates 17, which were prepared via cycloaddition of ethyl isocyanoacetate 16 and diarylimidoyl chlorides 15. Evaluation of these new target scaffolds in the AlphaScreenTM HIV-1 IN-LEDGF/p75 inhibition assay identified seventeen compounds exceeding the pre-defined 50% inhibitory threshold at 100 µM concentration. Further evaluation of these compounds in the HIV-1 IN strand transfer assay at 100 μM showed that none of the compounds (with the exception of 10a, 10l, and 11k, with marginal inhibitory percentages) were actively bound to the active site, indicating that they are selectively binding to the LEDGF/p75-binding pocket. In a cell-based HIV-1 antiviral assay, compounds 11a, 11b, 11g, and 11h exhibited moderate antiviral percentage inhibition of 33–45% with cytotoxicity (CC50) values of >200 µM, 158.4 µM, >200 µM, and 50.4 µM, respectively. The antiviral inhibitory activity displayed by 11h was attributed to its toxicity. Upon further validation of their ability to induce multimerization in a Western blot gel assay, compounds 11a, 11b, and 11h appeared to increase higher-order forms of IN.

  设计和合成了两组新型的1,5-二芳基-1H-咪唑-4-羧酸类化合物10和羧酰肼类化合物11，它们是从它们对应的酯中间体17合成的，这些酯中间体是通过乙酰氰乙酸乙酯16和二芳基咪唑基氯化物15的环加成反应制备的。在AlphaScreenTM HIV-1 IN-LEDGF/p75抑制试验中评估了这些新的目标结构，发现17种化合物在100微米浓度下超过了预定义的50%抑制阈值。在100微米浓度下对这些化合物进行HIV-1 IN链转移试验的进一步评估显示，除了10a、10l和11k（具有边缘抑制百分比）之外，其他化合物均未活跃地结合到活性位点，表明它们选择性地结合到LEDGF/p75结合口袋。在基于细胞的HIV-1抗病毒试验中，化合物11a、11b、11g和11h表现出中等抗病毒百分比抑制率为33-45%，细胞毒性（CC50）值分别为>200微米、158.4微米、>200微米和50.4微米。11h表现出的抗病毒抑制活性归因于其毒性。通过在Western blot凝胶试验中验证它们诱导多聚体形成的能力，化合物11a、11b和11h似乎增加了IN的高阶形式。