1-benzyl-2-benzylidene-1-(4-methoxyphenyl)hydrazine | 28772-59-0

• 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-(4-methoxyphenyl)hydrazine
• 英文别名: N-Benzyliden-N'-benzyl-N'-(4-methoxyphenyl)-hydrazin；Benzaldehyd-(benzyl-4-methoxyphenyl-hydrazon)；Benzaldehyde, 2-(4-methoxyphenyl)-2-(phenylmethyl)hydrazone；N-benzyl-N-(benzylideneamino)-4-methoxyaniline
• CAS: 28772-59-0
• 化学式: C₂₁H₂₀N₂O
• 分子量: 316.403
• InChiKey: WZGORYIROLTFMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-benzylidene-1-(4-methoxyphenyl)hydrazine 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以70%的产率得到1-benzyl-5-methoxy-2-phenyl-1H-benzo[d]imidazole
  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-(4-methoxyphenyl)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

• 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.
• 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.