1-(4-nitrophenyl)-4-(phenethyl)piperazine | 329004-00-4

• 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-nitrophenyl)-4-(phenethyl)piperazine
• 英文别名: Cambridge id 5431401；1-(4-nitrophenyl)-4-(2-phenylethyl)piperazine
• CAS: 329004-00-4
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: HIAJFTBTNVXHGH-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  479.8±45.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-4-(phenethyl)piperazine 在 盐酸 、 tin 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 以80%的产率得到4-(4-phenethylpiperazin-1-yl)phenylamine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new arylpiperazines N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives: Putative role of 5-HT1A receptors

  摘要：

  In an attempt to design novel 5-HT1A agonists/partial agonists, based on an arylpiperazine nucleus, a series of N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives were synthesized and biologically tested. The anxiolytic effect of the compounds was investigated employing the Elevated plus Maze (EPM) task. On the basis of in vivo functional test, compound 1c (3 mg/kg) and 4c (3 mg/kg) induced significant increments in open arm entries and time on EPM as compared to Buspirone. The anxiolytic effects of compounds 1c and 4c were effectively antagonized by WAY-100635, a 5-HT1A receptor antagonist (0.5 mg/kg). Furthermore, we have also evaluated the concentration of 5-HT in the brain tissue using HPLC with fluorescent detection. Our result showed that serotonin levels were significantly decreased by similar to 38% (p < 0.001) and similar to 32% (p < 0.001) after acute administration of compounds 1c and 4c, respectively. These findings suggest that the anxiolytic like activity of these new arylpiperazines is mediated via 5-HT1A receptors in the brain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.043
• 作为产物：
  描述：

  1-(4-硝基苯基)哌嗪 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以80%的产率得到1-(4-nitrophenyl)-4-(phenethyl)piperazine
  参考文献：
  名称：

  4-芳酰基（和芳基）-1-芳烷基哌嗪的合成及III类抗心律失常活性。

  摘要：

  描述了几种4-芳酰基（和芳基）-1-芳烷基哌嗪和哌啶衍生物的合成和体外Ⅲ类抗心律失常活性。在该系列中鉴定出的几种有效化合物中，RWJ-28810（3）的EC20为3 nM，被列为最有效的（体外）化合物之一。

  DOI：

  10.1016/s0960-894x(00)00581-3

文献信息

• Ruthenium Catalyzed Regioselective β‐C( <i>sp</i> ³ )−H Functionalization of <i>N</i> ‐Alkyl‐ <i>N′</i> ‐ <i>p–</i> nitrophenyl Substituted Piperazines using Aldehydes as Alkylating Agents
  作者：V. Murugesh、Apurba Ranjan Sahoo、Mathieu Achard、Gangavaram V. M. Sharma、Christian Bruneau、Surisetti Suresh

  DOI：10.1002/adsc.202001060

  日期：2021.1.19

  Herein, we disclose a ruthenium‐catalyzed regioselective β‐C(sp3)−H bond functionalization on the piperazine core using aldehydes as alkylating agents. The present transformation appears to go through the dehydrogenation of the piperazine to propagate to enamine in situ, followed by nucleophilic addition to the aldehyde and hydrogenation to result in the regioselective β‐C(sp3)−H alkylation. A variety

  在本文中，我们公开了使用醛类作为烷基化剂在哌嗪核上进行钌催化的区域选择性β-C（sp 3）-H键官能化。目前的转化似乎是通过哌嗪的脱氢反应，使其原位扩散为烯胺，然后向醛中进行亲核加成反应，然后进行氢化反应，从而形成区域选择性的β-C（sp 3）-H烷基化反应。多种芳族，杂芳族，脂族醛的被用于的C-3烷基化ñ -烷基- N' - p硝基苯基取代的哌嗪。
• Synthesis and pharmacological evaluation of new arylpiperazines N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives: Putative role of 5-HT1A receptors
  作者：Manisha Khatri、Santosh Kumar Rai、Sameena Alam、Anjana Vij、Manisha Tiwari

  DOI：10.1016/j.bmc.2009.01.043

  日期：2009.3

  In an attempt to design novel 5-HT1A agonists/partial agonists, based on an arylpiperazine nucleus, a series of N-4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives were synthesized and biologically tested. The anxiolytic effect of the compounds was investigated employing the Elevated plus Maze (EPM) task. On the basis of in vivo functional test, compound 1c (3 mg/kg) and 4c (3 mg/kg) induced significant increments in open arm entries and time on EPM as compared to Buspirone. The anxiolytic effects of compounds 1c and 4c were effectively antagonized by WAY-100635, a 5-HT1A receptor antagonist (0.5 mg/kg). Furthermore, we have also evaluated the concentration of 5-HT in the brain tissue using HPLC with fluorescent detection. Our result showed that serotonin levels were significantly decreased by similar to 38% (p < 0.001) and similar to 32% (p < 0.001) after acute administration of compounds 1c and 4c, respectively. These findings suggest that the anxiolytic like activity of these new arylpiperazines is mediated via 5-HT1A receptors in the brain. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and class III type antiarrhythmic activity of 4-aroyl (and aryl)-1-aralkylpiperazines
  作者：Ramesh M. Kanojia、Joseph J. Salata、Jack Kauffman

  DOI：10.1016/s0960-894x(00)00581-3

  日期：2000.12

  The synthesis and in vitro Class III antiarrhythmic activity of several 4-aroyl (and aryl)-1-aralkylpiperazine and piperidine derivatives are described. Among several potent compounds identified in the series, RWJ-28810 (3), with its EC20 of 3 nM, ranks as one of the most potent (in vitro) compounds reported.

  描述了几种4-芳酰基（和芳基）-1-芳烷基哌嗪和哌啶衍生物的合成和体外Ⅲ类抗心律失常活性。在该系列中鉴定出的几种有效化合物中，RWJ-28810（3）的EC20为3 nM，被列为最有效的（体外）化合物之一。