1,4-bis[(3-trifluoromethyl)phenyl]piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1,4-bis[(3-trifluoromethyl)phenyl]piperazine
• 英文别名: 1,4-bis(3-trifluoromethyl-phenyl)piperazine；1,4-Bis[3-(trifluoromethyl)phenyl]piperazine
• 化学式: C₁₈H₁₆F₆N₂
• 分子量: 374.329
• InChiKey: WIRNLAPILLQLRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  哌嗪 、 间氯三氟甲苯 在 2-甲基-2-丁醇 2,2'-联吡啶 、 nickel diacetate 、 sodium hydride 、 苯乙烯 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以82%的产率得到1,4-bis[(3-trifluoromethyl)phenyl]piperazine
  参考文献：
  名称：

  镍催化仲二胺的选择性N-芳基化或N，N'-二芳基化

  摘要：

  描述了使用与2,2'-联吡啶缔合的Ni（0）的催化剂组合，从相应的二胺和芳基氯化物选择性合成N-芳基或N，N'-二芳基哌嗪和三亚甲基（双）哌啶。Ni / 2，2'-联吡啶催化剂对于哌嗪的顺序芳基化也是有效的。报道了新型和不对称的1，4-二芳基哌嗪的制备。

  DOI：

  10.1016/s0040-4020(02)00750-0

文献信息

• Nickel-catalysed selective N-arylation or N,N′-diarylation of secondary diamines
  作者：Eric Brenner、Raphaël Schneider、Yves Fort

  DOI：10.1016/s0040-4020(02)00750-0

  日期：2002.8

  synthesis of N-aryl or N,N′-diaryl piperazines and trimethylene(bis)piperidines from the corresponding diamines and aryl chlorides using a catalyst combination of Ni(0) associated to 2,2′-bipyridine is described. The Ni/2,2′-bipyridine catalyst is also effective for the sequential arylation of piperazine. The preparation of novel and unsymmetrical 1,4-diaryl piperazines is reported.

  描述了使用与2,2'-联吡啶缔合的Ni（0）的催化剂组合，从相应的二胺和芳基氯化物选择性合成N-芳基或N，N'-二芳基哌嗪和三亚甲基（双）哌啶。Ni / 2，2'-联吡啶催化剂对于哌嗪的顺序芳基化也是有效的。报道了新型和不对称的1，4-二芳基哌嗪的制备。
• Nickel-mediated amination chemistry. Part 2: Selective N-arylation or N,N′-diarylation of piperazine
  作者：Eric Brenner、Raphaël Schneider、Yves Fort

  DOI：10.1016/s0040-4039(00)00277-x

  日期：2000.4

  The 2,2'-bipyridine liganded Ni catalyst has revealed a good selectivity in the mono arylation of piperazine starting from aryl chlorides allowing a selective and efficient synthesis of N-arylpiperazines using stoichiometric amounts of reagents. The preparation of N,N'-diaryl substituted piperazines is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst
  作者：Masakazu Nishiyama、Toshihide Yamamoto、Yasuyuki Koie

  DOI：10.1016/s0040-4039(97)10659-1

  日期：1998.2

  A Pd/P(t-Bu)(3) catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines could be prepared using this catalyst. Turnover numbers up to 6400mol/mol have been obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides
  作者：Georg Manolikakes、Andrei Gavryushin、Paul Knochel

  DOI：10.1021/jo702219f

  日期：2008.2.1

  A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)2, 1 mol% of 3,5,6,8-tetrabromo-1, 10-phenanthroline, and polymethythydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.