N-(piperidinylthiocarbonyl)-2-fluorobenzamide | 880579-48-6

• 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: N-(piperidinylthiocarbonyl)-2-fluorobenzamide
• 英文别名: 2-fluoro-N-(piperidine-1-carbothioyl)benzamide
• CAS: 880579-48-6
• 化学式: C₁₃H₁₅FN₂OS
• 分子量: 266.339
• InChiKey: XLBLQYJNXMZNCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  nickel(II) sulphate 、 N-(piperidinylthiocarbonyl)-2-fluorobenzamide 在 三乙胺 作用下， 以 乙醇 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)

  摘要：

  合成了 N-2-氟苯甲酰基哌啶-1-硫代亚胺酸（L2-）、N-4-氟苯甲酰基哌啶-1-硫代亚胺酸（L3-）、N-2-氟苯甲酰基吗啉-1-硫代亚胺酸（L5-）和 N-4-氟苯甲酰基吗啉-1-硫代亚胺酸（L6-）的 Ni(II) 配合物，并通过元素分析、傅立叶变换红外光谱和 1H-NMR 对其进行了表征。 通过 X 射线衍射测定了三种配体（HL2、HL3 和 HL6）和相应的 Ni(II) 复合物（[Ni(L2)2]、[Ni(L3)2] 和 [Ni(L6)2]）的晶体结构。研究了 Ni(II) 复合物和相应配体对灰霉病菌、毛霉属真菌、霉菌和轮枝霉菌的抗真菌活性。实验结果表明，配体及其配合物具有抗真菌能力。当对苯甲酰基上的氟被取代后，配体的抗真菌活性明显提高。此外，配体对真菌的抑制作用强于其配合物。HL6 的抗真菌能力特别强，与商用杀真菌剂氟康唑的抗真菌能力相似。

  DOI：

  10.3390/molecules181215737
• 作为产物：
  描述：

  邻氟苯甲酸 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 N-(piperidinylthiocarbonyl)-2-fluorobenzamide
  参考文献：
  名称：

  Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)

  摘要：

  合成了 N-2-氟苯甲酰基哌啶-1-硫代亚胺酸（L2-）、N-4-氟苯甲酰基哌啶-1-硫代亚胺酸（L3-）、N-2-氟苯甲酰基吗啉-1-硫代亚胺酸（L5-）和 N-4-氟苯甲酰基吗啉-1-硫代亚胺酸（L6-）的 Ni(II) 配合物，并通过元素分析、傅立叶变换红外光谱和 1H-NMR 对其进行了表征。 通过 X 射线衍射测定了三种配体（HL2、HL3 和 HL6）和相应的 Ni(II) 复合物（[Ni(L2)2]、[Ni(L3)2] 和 [Ni(L6)2]）的晶体结构。研究了 Ni(II) 复合物和相应配体对灰霉病菌、毛霉属真菌、霉菌和轮枝霉菌的抗真菌活性。实验结果表明，配体及其配合物具有抗真菌能力。当对苯甲酰基上的氟被取代后，配体的抗真菌活性明显提高。此外，配体对真菌的抑制作用强于其配合物。HL6 的抗真菌能力特别强，与商用杀真菌剂氟康唑的抗真菌能力相似。

  DOI：

  10.3390/molecules181215737

文献信息

• Crystal structures and antimicrobial activities of copper(II) complexes of fluorine-containing thioureido ligands
  作者：Huanhuan Liu、Wen Yang、Weiqun Zhou、Yunlong Xu、Juan Xie、Mengying Li

  DOI：10.1016/j.ica.2013.06.029

  日期：2013.8

  Cu(II) complexes with N-4-fluorobenzoylpiperidine-1-carbothioimidate (L1(-)), N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2(-)) and 2-fluorobenzoate (L3(-)) have been synthesized and characterized by elemental analysis, Fourier Transform infrared (FT-IR), Ultraviolet (UV) and fluorescence spectroscopy methods. The crystal structures of [Cu(L1)(2)], [Cu(L2)(2)] and [Cu-2(L3)(4)(DMF)(2)] (DMF: N,N-dimethylformamide) have been determined by X-ray diffraction method. The antimicrobial activities of the complexes against the bacteria (Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Shewanella sp.) and the fungi (Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp.) have been investigated comparing with the corresponding ligands. The experiments showed that the complexes had the stronger antibacterial and antifungal activities than the corresponding ligands had. (C) 2013 The Authors. Published by Elsevier B.V. All rights reserved.
• Synthesis, structures and antibacterial activities of benzoylthiourea derivatives and their complexes with cobalt
  作者：Wen Yang、Huanhuan Liu、Mengying Li、Fan Wang、Weiqun Zhou、Jianfen Fan

  DOI：10.1016/j.jinorgbio.2012.08.001

  日期：2012.11

  Four new thiocarbonyl fluorobenzamides and their complexes with cobalt have been synthesized and characterized by elemental analysis, FTIR, and H-1 NMR. Five crystal structures of the thioylbenzamides complexes of Co(PTCB)(3), Co(2FPTCB)(3), Co(4FPTCB)(3), Co(2FMTCB)(2) and Co(4FMTCB)(3) have been determined by X-ray diffraction. The antibacterial properties of these compounds against the bacteria, E. coli, Staphylococcus aureus, B. subtilis, P. aeruginosa, and Shewanella sp. were investigated. The experiments showed that both compounds and the complexes had the antibacterial activities against all of the studied bacteria. The thioylbenzamides had stronger controls for the bacteria of E. coli, S. aureus, B. subtilis and P. aeruginosa than their corresponding cobalt complexes. There was the contrary result against the bacteria of Shewanella sp. The para-substitution of fluorine atom increased antibacterial activities, while fluorine atom was substituted on ortho-benzoyl, the antibacterial activity weakened. The thioylbenzamides linked to piperidine instead of a morpholine group may increase the antibacterial activities. (c) 2012 Elsevier Inc. All rights reserved.
• Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)
  作者：Chun Li、Wen Yang、Huanhuan Liu、Mengying Li、Weiqun Zhou、Juan Xie

  DOI：10.3390/molecules181215737

  日期：——

  Ni(II) complexes with N-2-fluorobenzoylpiperidine-1-carbothioimidate (L2−), N-4-fluorobenzoylpiperidine-1-carbothioimidate (L3−), N-2-fluorobenzoylmorpholine- 1-carbothioimidate (L5−) and N-4-fluorobenzoylmorpholine-1-carbothioimidate (L6−) have been synthesized and characterized by elemental analysis, FTIR and 1H-NMR. The crystal structures of three ligands (HL2, HL3 and HL6) and the corresponding Ni(II) complexes ([Ni(L2)2], [Ni(L3)2] and [Ni(L6)2]) have been determined by X-ray diffraction. The antifungal activities of the Ni(II) complexes together and the corresponding ligands against the fungi Botrytis cinerea, Trichoderma spp., Myrothecium and Verticillium spp. have been investigated. The experimental results showed that the ligands and their complexes have antifungal abilities. When the fluorine was substituted on the para-benzoyl moiety, the antifungal activity of the ligands was obviously increased. Moreover, the ligands were stronger than their complexes in inhibiting fungal activities. The antifungal ability of HL6 is especially strong, and similar to that of the commercial fungicide fluconazole.

  合成了 N-2-氟苯甲酰基哌啶-1-硫代亚胺酸（L2-）、N-4-氟苯甲酰基哌啶-1-硫代亚胺酸（L3-）、N-2-氟苯甲酰基吗啉-1-硫代亚胺酸（L5-）和 N-4-氟苯甲酰基吗啉-1-硫代亚胺酸（L6-）的 Ni(II) 配合物，并通过元素分析、傅立叶变换红外光谱和 1H-NMR 对其进行了表征。 通过 X 射线衍射测定了三种配体（HL2、HL3 和 HL6）和相应的 Ni(II) 复合物（[Ni(L2)2]、[Ni(L3)2] 和 [Ni(L6)2]）的晶体结构。研究了 Ni(II) 复合物和相应配体对灰霉病菌、毛霉属真菌、霉菌和轮枝霉菌的抗真菌活性。实验结果表明，配体及其配合物具有抗真菌能力。当对苯甲酰基上的氟被取代后，配体的抗真菌活性明显提高。此外，配体对真菌的抑制作用强于其配合物。HL6 的抗真菌能力特别强，与商用杀真菌剂氟康唑的抗真菌能力相似。