1-benzyl-2-benzylidene-1-(p-tolyl)hydrazine | 28767-76-2

• 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-benzyl-2-benzylidene-1-(p-tolyl)hydrazine
• 英文别名: N-Benzyliden-N'-benzyl-N'-(4-methylphenyl)-hydrazin；N-Benzyl-N-p-tolyl-N'-benzyliden-hydrazin；benzaldehyde-(benzyl-p-tolyl-hydrazone)；Benzaldehyd-(benzyl-p-tolyl-hydrazon)；Benzaldehyde, 2-(4-methylphenyl)-2-(phenylmethyl)hydrazone；N-benzyl-N-(benzylideneamino)-4-methylaniline
• CAS: 28767-76-2
• 化学式: C₂₁H₂₀N₂
• 分子量: 300.403
• InChiKey: HKPALTUQHDUVQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-benzylidene-1-(p-tolyl)hydrazine 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到1-苄基-5-甲基-2-苯基苯并咪唑
  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：

  苯甲醛苯腙 在 sodium acetate 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 59.0h， 生成 1-benzyl-2-benzylidene-1-(p-tolyl)hydrazine
  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

• Construction of Trisubstituted Hydrazones via Base-Mediated Cascade Condensation <i>N</i>-Alkylation
  作者：Wentao Hao、Shuo Gao、Hongyi Cui、Ding Ding、Shaohua Jiang、Chunyan Zhang、Yuqi Ji、Guoying Zhang

  DOI：10.1021/acs.joc.3c02621

  日期：2024.2.16

  base-promoted tandem condensation N-alkylation reaction for the formation of trisubstituted hydrazones has been developed employing aldehydes and hydrazines with alkyl halides. Crucially, this reaction successfully overcomes chemoselectivity problems, allowing for the reaction of multiple components in a one-pot manner. Halo- and heterofunctional groups, as well as free hydroxyl and amino groups, are tolerated

  使用醛和肼与烷基卤，开发了一种实用的碱促进串联缩合N-烷基化反应，用于形成三取代腙。至关重要的是，该反应成功地克服了化学选择性问题，允许多种组分以一锅的方式进行反应。在该转化中可以耐受卤代和杂官能团以及游离羟基和氨基，从而以良好到优异的收率产生各种三取代腙。
• Busch; Lang, Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 144, p. 291,305
  作者：Busch、Lang

  DOI：——

  日期：——
• A one-pot synthesis of bisarylhydrazones by Cu(I)-catalyzed aerobic oxidation
  作者：Jiu-Rong Hu、Wan-Jia Zhang、Da-Gui Zheng

  DOI：10.1016/j.tet.2013.08.073

  日期：2013.11

  An efficient Cu(I)-catalyzed one-pot synthesis of N-substituted (or NH) bisarylhydrazones is reported. A further cyclization reaction could occur towards the synthesis of benzimidazoles or triazoles with elevated temperature. A plausible alkylation-oxidation-alkylation mechanism is proposed based on experimental results and literature. (C) 2013 Elsevier Ltd. All rights reserved.
• Votocek; Allan, Collection of Czechoslovak Chemical Communications, 1936, vol. 8, p. 313,314
  作者：Votocek、Allan

  DOI：——

  日期：——
• Copper-Mediated Synthesis of Substituted 2-Aryl-<i>N</i>-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation
  作者：Murali Mohan Guru、Md Ashif Ali、Tharmalingam Punniyamurthy

  DOI：10.1021/jo2005632

  日期：2011.7.1

  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.