1-(苯基甲基)-4-[3-(三氟甲基)苯基]-哌嗪 | 36824-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(苯基甲基)-4-[3-(三氟甲基)苯基]-哌嗪
• 英文名称: benzyl-4-[3-(trifluoromethyl)phenyl]piperazine
• 英文别名: 1-Benzyl-4-[3-(trifluoromethyl)phenyl]piperazine
• CAS: 36824-73-4
• 化学式: C₁₈H₁₉F₃N₂
• mdl: MFCD01652457
• 分子量: 320.357
• InChiKey: MUULAWDTOQZBBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2’-(苄基亚氨基)二乙醇 、 间氨基三氟甲苯 在 (C₆H₃N(CH₂NMe₂)2)Ru(PPh₃)(O₃SCF₃) 作用下， 以 1,4-二氧六环 为溶剂， 以29%的产率得到1-(苯基甲基)-4-[3-(三氟甲基)苯基]-哌嗪
  参考文献：
  名称：

  Ruthenium-Complex-Catalyzed N-(Cyclo)alkylation of Aromatic Amines with Diols. Selective Synthesis of N-(ω-Hydroxyalkyl)anilines of Type PhNH(CH₂)_nOH and of Some Bioactive Arylpiperazines

  摘要：

  A new class of well-defined neutral mono-, and dicationic ruthenium(II) complexes containing a neutral terdentate donor system [C5H3N(CH2E)(2)-2,6] (E = PPh2 (PNP) or NMe2 (NN'N)) has been found effective as catalyst precursor in N-(cyclo)alkylation reactions of aromatic amines with diols Y(CH2CH2OH)(2) (Y = CH2, NR). With these catalysts, N-phenylpiperidine is synthesized from aniline and 1,5-pentanediol in 85% yield (at 180 degrees C for 24 h in 1,4-dioxane). With neutral RuCl2(NN'N)(PPh3) as a catalyst precursor, aniline can be selectively N-monoalkylated with diols of the type HO(CH2)(n)OH (n = 4-6, 10) to give N-(n-hydroxyalkyl)anilines in 40-75% yield. To our knowledge, this represents the first useful catalytic route to this type of compounds. The new catalysts can also be used in the synthesis of arylpiperazines. For example, N-phenyl-N'-methylpiperazine is obtained from aniline and MeN(CH2CH2OH)(2) in yields up to 34%. N-[m-(Trifluoromethyl)phenyl]-N'-methylpiperazine, TFMPMP, is successfully produced from m-(trifluoromethyl)aniline and MeN(CH2CH2OH)(2) in 44% yield using monocationic [RuOTf(NN'N)(PPh3)]OTf as the catalyst precursor. A mechanism for the N-(cyclo)alkylation reaction is proposed.

  DOI：

  10.1021/jo972260d

文献信息

• Synthesis of N-alkyl-N′-aryl-piperazines via copper-catalyzed C–N bond formation
  作者：Issa Yavari、Mohammad J. Bayat、Majid Ghazanfarpour-Darjani

  DOI：10.1016/j.tetlet.2014.08.045

  日期：2014.10

  An efficient copper-catalyzed tandem synthesis of N-alkyl-N'-aryl-piperazines from 1,4-diazabicyclo[2.2.2]octane, alkyl halides, and aryl halides in the presence of copper(I) iodide and potassium tert-butoxide in DMSO is described. (C) 2014 Published by Elsevier Ltd.
• US5731438A
  申请人：——

  公开号：US5731438A

  公开（公告）日：1998-03-24
• US5780241A
  申请人：——

  公开号：US5780241A

  公开（公告）日：1998-07-14
• US5798360A
  申请人：——

  公开号：US5798360A

  公开（公告）日：1998-08-25
• US5817489A
  申请人：——

  公开号：US5817489A

  公开（公告）日：1998-10-06