4-methyl-benzaldehyde p-tolylhydrazone | 65452-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-benzaldehyde p-tolylhydrazone
• 英文别名: p-Toluylaldehyd-p-tolylhydrazon；4-Methyl-benzaldehyd-p-tolylhydrazon；4-methyl-N-[(4-methylphenyl)methylideneamino]aniline
• CAS: 65452-76-8
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: DRLMWRKCAFDGGI-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  355.2±35.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methyl-benzaldehyde p-tolylhydrazone 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 31.0h， 生成 1-Benzyl-5-methyl-2-(4-methylphenyl)-1H-benzimidazole
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632
• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 生成 4-methyl-benzaldehyde p-tolylhydrazone
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632

文献信息

• Facile synthesis of pyrazoles by iron-catalyzed regioselective cyclization of hydrazone and 1,2-diol under ligand-free conditions
  作者：Niranjan Panda、Subhadra Ojha

  DOI：10.1016/j.jorganchem.2018.02.043

  日期：2018.4

  A facile synthesis of pyrazoles by the cyclization of hydrazones and 1,2-diols was described. In the presence of ferric nitrate, the reaction occurs under neat conditions and makes the use of potassium persulfate to oxidize the diol to α-hydroxy carbaldehyde for the reaction with hydrazones to produce 1,3- and 1,3,5-substituted pyrazoles selectively. The overall regioselective transformation occurs

  描述了通过和1,2-二醇的环化容易地合成吡唑。在硝酸铁存在下，反应在纯净条件下发生，并利用过硫酸钾将二醇氧化为α-羟基甲醛，与反应生成选择性生成1,3-和1,3,5-取代的吡唑。整体区域选择性转化在无配体的温和条件下甚至在空气中一锅进行。
• Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes
  作者：Vladimir A. Motornov、Andrey A. Tabolin、Yulia V. Nelyubina、Valentine G. Nenajdenko、Sema L. Ioffe

  DOI：10.1002/ejoc.202000841

  日期：2020.8.31

  Three‐component one pot assembly of 4‐fluoropyrazoles is described. The method involves formal oxidative [3+2]‐annulation between elusive fluoroalkynes and azomethine imines.

  描述了4-氟吡唑的三组分一锅组件。该方法涉及难以捉摸的氟代炔烃和偶氮甲亚胺之间的正式氧化[3 + 2]-环化反应。
• Microwave assisted one-pot tandem three-component synthesis of 2,4,5-triary1-2-4-dihydro-3H-1,2,4-triazol-3-one derivatives
  作者：Bagher Mohammadi、Mehdi Adib

  DOI：10.1016/j.cclet.2013.12.018

  日期：2014.4

  This work described a one-pot tandem three-component synthesis of 2,4,5-triaryl-2,4-dihydro-3H-1,2,4-triazol-3-ones using a simple reaction between phenylhydrazines, benzaldehydes and phenyl isocyanates under microwave irradiation and solvent-free conditions in good to excellent yields.

  这项工作描述了使用苯肼，苯甲醛和苯甲醛之间的简单反应，一锅串联的三组分合成2,4,5-三芳基-2,4-二氢-3 H -1,2,4-三唑-3-酮。在微波辐射和无溶剂条件下，异氰酸苯酯的收率良好至优异。
• Antimycobacterial Assessment and Microwave-assisted Synthesis of 2-aryl- 3-(4-methylphenylamino)thiazolidin-4-one Derivatives
  作者：Saad Alghamdi、Mehnaz Kamal、Mohammad Asif

  DOI：10.2174/1570178618666210302160625

  日期：2022.3

  This article reports the microwave-assisted synthesis, characterization, and evaluation of some -4-one derivatives (2a-2h) for their in-vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv strain by microplate Alamar blue assay (MABA) method. All these final compounds (2a-2h) were synthesized from Schiff’s bases, 1-arylidene-2-(4-methylphenyl)hydrazines (1a-1h), and thioglycolic acid by using zinc chloride as a catalyst. Compounds (1a-1h) were synthesized from the reaction of 4-methylhydrazine and appropriate aromatic aldehydes by Schiff’s reaction. Among the target compounds, 2-(4-ethoxyphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2f) and 2-(4-ethylphenyl)-3-(4-methylarylamino)thiazolidin-4-one (2g) were promising with a minimum inhibitory concentration (MIC) of 12.5 μg/mL against M. tuberculosisH37Rv. Based on the preliminary results, compounds 2f and 2g were considered as lead compounds for the advanced design and development of antimycobacterial agents.

  摘要：本文报道了一些-4-酮衍生物（2a-2h）的微波辅助合成、表征和评估它们在体外对结核分枝杆菌H37Rv菌株的抗菌活性，采用微孔板AlaMAr蓝色试验（MABA）方法。所有这些最终化合物（2a-2h）都是使用氯化锌作为催化剂，从席夫碱，1-芳基亚甲基-2-（4-甲基苯基）腙（1a-1h）和巯基乙酸合成的。化合物（1a-1h）是由4-甲基肼和适当的芳香醛反应制得的。在目标化合物中，2-（4-乙氧基苯基）-3-（4-甲基芳基氨基）噻唑啉-4-酮（2f）和2-（4-乙基苯基）-3-（4-甲基芳基氨基）噻唑啉-4-酮（2g）是有前途的，对M. tuberculosis H37Rv的最小抑制浓度（MIC）为12.5 μg/mL。根据初步结果，化合物2f和2g被认为是先导化合物，用于抗结核分枝杆菌药物的先进设计和开发。
• Ce-catalyzed regioselective synthesis of pyrazoles from 1,2-diols <i>via</i> tandem oxidation and C–C/C–N bond formation
  作者：Chandan Kumar Pal、Ashis Kumar Jena

  DOI：10.1039/d2ob01996e

  日期：——

  novel and efficient cerium-catalyzed tandem oxidation and intermolecular ring cyclization of vicinal diols with hydrazones has been achieved for the regioselective synthesis of pyrazole derivatives. The corresponding 1,3-di- and 1,3,5-trisubstituted pyrazoles were obtained in moderate to excellent yields. The reaction has the advantages of mild conditions, easily available starting materials, broad substrate

  已经实现了一种新型高效的铈催化串联氧化和邻位二醇与腙的分子间环化，用于吡唑衍生物的区域选择性合成。相应的 1,3-二和 1,3,5-三取代吡唑以中等到极好的产率获得。该反应条件温和、起始原料易得、底物适用范围广、官能团耐受性好。