N,N-bis(3-(thiophene-2-carboxamido)propyl)piperazine | 547722-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: N,N-bis(3-(thiophene-2-carboxamido)propyl)piperazine
• 英文别名: 1,4-bis[3-(2-thiophenecarboxamido)propyl]piperazine；N,N'-bis((thiophene-2-carboxamido)propyl)piperazine；N-[3-[4-[3-(thiophene-2-carbonylamino)propyl]piperazin-1-yl]propyl]thiophene-2-carboxamide
• CAS: 547722-97-4
• 化学式: C₂₀H₂₈N₄O₂S₂
• mdl: MFCD03399096
• 分子量: 420.6
• InChiKey: BUWVHZIRQGMQLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-bis(3-(thiophene-2-carboxamido)propyl)piperazine 、 copper dichloride 以 甲醇 为溶剂， 生成 C₂₀H₂₈CuN₄O₂S₂⁽²⁺⁾*2Cl^(1-)
  参考文献：
  名称：

  Synthesis, characterization, and antibacterial activity of the ligands including thiophene/furan ring systems and their Cu(II), Zn(II) complexes

  摘要：

  Carboxamide complexes having general formula as [ML]Cl-2 center dot nH(2)O (where M = Cu(II), Zn(II); n = 0, 1/2) were synthesized using heterocyclic carboxamide ligands: 1,4-bis[3-(2-thiophenecarboxamido)propyl]piperazine (L-1) and 1,4-bis[3-(2-furancarboxamido) propyl]piperazine (L-2). Their structures were characterized with elemental analysis, molar conductivity, magnetic susceptibility, and spectral methods (H-1-NMR, C-13-NMR, FT-IR, LC-MS). TGA and DTA curves were also performed. The structure-activity relationship for the ligands was investigated using PM3 semi-empirical method. The antibacterial activities of the carboxamides and their complexes were investigated against bacteria; Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 11230, Bacillus magaterium RSKK 5117, B. cereus RSKK 863, Salmonella enteritidis ATCC 13076, B. subtilis RSKK 244 using microdilution method.

  DOI：

  10.1007/s00044-011-9878-8
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 1,4-双(3-氨基丙基)哌嗪 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到N,N-bis(3-(thiophene-2-carboxamido)propyl)piperazine
  参考文献：
  名称：

  Synthesis, Spectroscopic Studies and Crystal Structure of N,N′-bis((thiophene-2-carboxamido)propyl)piperazine

  摘要：

  由噻吩-2-甲酰氯和 1,4-双(3-氨基丙基)哌嗪反应合成了一种新的多叉配体 N,N′-双((噻吩-2-甲酰胺)丙基)哌嗪。通过元素分析、傅立叶变换红外光谱、1H-NMR 和 13C-NMR 光谱技术对标题化合物进行了表征。标题化合物（C20H30N4O2S2Cl2）的晶体结构也已通过 X 射线分析确定。标题化合物在单斜空间群 P21/c 中结晶，a = 9.768(1), b = 12.895(1), c = 10.083(1) Å, β = 115.12(1)°, V = 1149.9(2) Å3, D x = 1.直接法求解了晶体结构，并通过全矩阵最小二乘法对 2,786 个观察到的反射进行了细化，得到 R = 0.039 [I > 2σ (I)]。我们合成了 (N,N'-双((噻吩-2-羧基氨基)丙基)哌嗪) 分子，并利用傅立叶变换红外光谱、13C NMR 和 1H-NMR 光谱以及晶体学技术研究了其分子结构。

  DOI：

  10.1007/s10870-007-9302-x

文献信息

• Synthesis, characterization, and antibacterial activity of the ligands including thiophene/furan ring systems and their Cu(II), Zn(II) complexes
  作者：Ayla Balaban Gündüzalp、Neslihan Özbek、Nurcan Karacan

  DOI：10.1007/s00044-011-9878-8

  日期：2012.11

  Carboxamide complexes having general formula as [ML]Cl-2 center dot nH(2)O (where M = Cu(II), Zn(II); n = 0, 1/2) were synthesized using heterocyclic carboxamide ligands: 1,4-bis[3-(2-thiophenecarboxamido)propyl]piperazine (L-1) and 1,4-bis[3-(2-furancarboxamido) propyl]piperazine (L-2). Their structures were characterized with elemental analysis, molar conductivity, magnetic susceptibility, and spectral methods (H-1-NMR, C-13-NMR, FT-IR, LC-MS). TGA and DTA curves were also performed. The structure-activity relationship for the ligands was investigated using PM3 semi-empirical method. The antibacterial activities of the carboxamides and their complexes were investigated against bacteria; Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 11230, Bacillus magaterium RSKK 5117, B. cereus RSKK 863, Salmonella enteritidis ATCC 13076, B. subtilis RSKK 244 using microdilution method.
• Synthesis, Spectroscopic Studies and Crystal Structure of N,N′-bis((thiophene-2-carboxamido)propyl)piperazine
  作者：Ayla Balaban、Naki Çolak、Hüseyin Ünver、Birgül Erk、Tahsin Nuri Durlu、D. Mehmet Zengin

  DOI：10.1007/s10870-007-9302-x

  日期：2008.5

  A new multidentate ligand N,N′-bis((thiophene-2-carboxamide)propyl)piperazine has been synthesized from the reaction of thiophene-2-carbonylchloride and 1,4-bis(3-aminopropyl)piperazine. The title compound has been characterized by elemental analysis, FT-IR, 1H-NMR and 13C-NMR spectroscopic techniques. The crystal structure of the title compound (C20H30N4O2S2Cl2) has also been determined by X-ray analysis. The title compound crystallize in the monoclinic space group P21/c with a = 9.768(1), b = 12.895(1), c = 10.083(1) Å, β = 115.12(1)°, V = 1149.9(2) Å3, D x = 1.425 g cm−3 and Z = 2. The crystal structure was solved by direct methods and refined by full-matrix least squares to a find R = 0.039 [I > 2σ (I)] for 2,786 observed reflections. The (N,N’–bis((thiophene-2- carboxamido)propyl)piperazine) molecule has been synthesized and its molecule structure has been investigated by using , FT-IR, 13C NMR and 1H-NMR spectroscopic and crystallographic techniques.

  由噻吩-2-甲酰氯和 1,4-双(3-氨基丙基)哌嗪反应合成了一种新的多叉配体 N,N′-双((噻吩-2-甲酰胺)丙基)哌嗪。通过元素分析、傅立叶变换红外光谱、1H-NMR 和 13C-NMR 光谱技术对标题化合物进行了表征。标题化合物（C20H30N4O2S2Cl2）的晶体结构也已通过 X 射线分析确定。标题化合物在单斜空间群 P21/c 中结晶，a = 9.768(1), b = 12.895(1), c = 10.083(1) Å, β = 115.12(1)°, V = 1149.9(2) Å3, D x = 1.直接法求解了晶体结构，并通过全矩阵最小二乘法对 2,786 个观察到的反射进行了细化，得到 R = 0.039 [I > 2σ (I)]。我们合成了 (N,N'-双((噻吩-2-羧基氨基)丙基)哌嗪) 分子，并利用傅立叶变换红外光谱、13C NMR 和 1H-NMR 光谱以及晶体学技术研究了其分子结构。