3-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]propanenitrile | 4921-06-6

• 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: 3-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]propanenitrile
• 英文别名: 3-[4-(3-trifluoromethylphenyl)-piperazin-1-yl]-propionitrile；3-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-propionitrile；1-(2-Cyanoethyl)-4-piperazin；3-{4-[3-(Trifluoromethyl)phenyl]piperazin-1-yl}propanenitrile；3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propanenitrile
• CAS: 4921-06-6
• 化学式: C₁₄H₁₆F₃N₃
• 分子量: 283.296
• InChiKey: ZPOGGEALUFDQTG-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C(Solv: water (7732-18-5); isopropanol (67-63-0))
• 沸点：
  399.0±42.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]propanenitrile 在 sodium azide 、 三乙胺盐酸盐 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 58.0h， 生成 (2R,3S)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)-3-[5-[2-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]tetrazol-1-yl]butan-2-ol
  参考文献：
  名称：

  Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

  摘要：

  A series of (2 R, 3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazo-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yi]-ethyl}-tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12mug/mL for C. albicans, C albicans V-01-191A-261 (resistant strain); 0.25mug/mL for C tropicalis, C parapsilosis ATCC 22019 and C krusei and MIC value of 0.5 mug/mL for C glabrata, C krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5 mug/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25 mug/mL) against C neoformans. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.014
• 作为产物：
  描述：

  丙烯腈 、 1-(3-三氟甲基苯基)哌嗪 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以89.43%的产率得到3-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]propanenitrile
  参考文献：
  名称：

  Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

  摘要：

  A series of (2 R, 3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazo-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yi]-ethyl}-tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12mug/mL for C. albicans, C albicans V-01-191A-261 (resistant strain); 0.25mug/mL for C tropicalis, C parapsilosis ATCC 22019 and C krusei and MIC value of 0.5 mug/mL for C glabrata, C krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5 mug/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25 mug/mL) against C neoformans. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.014

文献信息

• Solventless microwave assisted protocol for synthesis of arylalkylpiperazines using Cs-base
  作者：Alain Gamal Giuglio-Tonolo、Thierry Terme、Patrice Vanelle

  DOI：10.1039/b812801d

  日期：——

  A series of some arylalkylpiperazines was prepared in good yields under microwave irradiation in dry media conditions using CsOH with high chemo- and regioselectivity.

  在干燥介质条件下，利用CsOH在微波辐射下制备了一系列取代芳基烷基哌嗪，获得了较高的产率，并且具有良好的化学选择性和区域选择性。