1-(4-methoxybenzylidene)-2-p-tolylhydrazine | 2829-30-3

• 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: 1-(4-methoxybenzylidene)-2-p-tolylhydrazine
• 英文别名: 4-methoxy-benzaldehyde p-tolylhydrazone；Anisal-p-tolylhydrazin；Anisaldehyd-p-tolylhydrazon；4-Methoxy-benzaldehyd-p-tolylhydrazon；N-[(4-methoxyphenyl)methylideneamino]-4-methylaniline
• CAS: 2829-30-3
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: QWGVQOCLXBFOFG-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  378.4±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzylidene)-2-p-tolylhydrazine 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 31.5h， 生成 1-benzyl-2-(p-methoxyphenyl)-5-methylbenzimidazole
  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 1-(4-methoxybenzylidene)-2-p-tolylhydrazine
  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

• Parallel Synthesis of Pyrazolineson Soluble Polymer Support
  作者：Yan-Guang Wang、Jian Zhang、Xu-Feng Lin、Han-Feng Ding

  DOI：10.1055/s-2003-40863

  日期：——

  An efficient and rapid parallel liquid-phase synthesis of pyrazolines has been developed. The one-pot three-components reaction of polyethylene glycol (PEG)-supported acrylate 1, aldehyde 2 and aryl hydrazine 3 in the presence of chloramine-T in methanol gave the corresponding PEG-supported pyrazolines 5. Cleavage from the support under mild conditions afforded pyrazolines 6 in good yields (69-91%)

  已开发出一种高效且快速的吡唑啉平行液相合成方法。聚乙二醇 (PEG) 负载的丙烯酸酯 1、醛 2 和芳基肼 3 在甲醇中氯胺-T 存在下的一锅三组分反应得到相应的 PEG 负载的吡唑啉 5。在温和条件下从载体上裂解以良好的产率 (69-91%) 和高纯度 (91-100%) 提供吡唑啉 6。
• 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。
• Convenient generation of 1,3-dipolar nitrilimines and [3 + 2] cycloaddition for the synthesis of spiro compounds
  作者：Mei-Jun Zhu、Rong Ye、Wen-Jing Shi、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.tetlet.2022.154186

  日期：2022.11

  In the presence of 2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as an oxidizer, the domino [3 + 2] cycloaddition reaction of aldohydrazones with 2-arylidene-1,3-indnaediones or 5-arylidene-1,3-dimethylbarbituric acids in acetonitrile at 80 °C afforded functionalized spiro[indene-2,4′-pyrazoles]-1,3-diones or 2,3,7,9-tetraazaspiro[4.5]dec-1-ene-6,8,10-triones in satisfactory yields. This reaction

  在 2,2,6,6-四甲基哌啶-1-基)氧基 (TEMPO) 作为氧化剂存在下，醛腙与 2-亚芳基-1,3-茚二酮或 5- 的多米诺 [3 + 2] 环加成反应亚芳基-1,3-二甲基巴比妥酸在乙腈中于 80 °C 提供官能化螺[茚-2,4'-吡唑]-1,3-二酮或 2,3,7,9-四氮杂螺[4.5]dec-1- ene-6,8,10-triones 的收率令人满意。该反应被认为是通过原位产生反应性1,3-偶极腈亚胺及其与环状亲偶极体的连续1,3-偶极环加成反应进行的。因此，成功开发了一种新的方便的活性偶极腈亚胺合成方法。
• 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。
• Padoa; Graziani, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1909, vol. <5> 18 II, p. 272,273
  作者：Padoa、Graziani

  DOI：——

  日期：——