2,6-bis{[N-butyl-N′-methylene]triazole-2-thione}pyridine | 1375075-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-bis{[N-butyl-N′-methylene]triazole-2-thione}pyridine
• 英文别名: 2,6-bis(N-(n-butyl)-N'-methylenetriazole-2-thione)pyridine；2-Butyl-4-[[6-[(1-butyl-5-sulfanylidene-1,2,4-triazol-4-yl)methyl]pyridin-2-yl]methyl]-1,2,4-triazole-3-thione；2-butyl-4-[[6-[(1-butyl-5-sulfanylidene-1,2,4-triazol-4-yl)methyl]pyridin-2-yl]methyl]-1,2,4-triazole-3-thione
• CAS: 1375075-12-9
• 化学式: C₁₉H₂₇N₇S₂
• 分子量: 417.602
• InChiKey: YZDDPFOLTNIZEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis{[N-butyl-N′-methylene]triazole-2-thione}pyridine 、 copper dichloride 以 二氯甲烷 为溶剂， 反应 20.0h， 以99%的产率得到bis[(η³-S,S,N)(2,6-bis){[N-butyl-N′-methylene]triazole-2-thione}pyridinecopper(II)tetrachlorocuprate]
  参考文献：
  名称：

  基于双硫酮前体的三配位 SNS-铜 (I) 配合物的合成、表征和计算研究

  摘要：

  一系列基于双咪唑基或双三唑基盐的三齿钳状配体（每个配体具有两个硫和一个氮供体（SNS））用 CuCl2 金属化，得到新的三齿 SNS 钳状铜（I）配合物 [(SNS)Cu] +。这些橙色配合物在铜中表现出三坐标伪三角平面几何形状。在这些铜 (I) 络合物的形成过程中，随着铜 (II) 盐前体转化为 Cu(I) [(SNS)Cu]+ 阳离子和 [CuCl4]2- 抗衡阴离子，观察到歧化。[(SNS)Cu]+ 配合物通过单晶 X 射线衍射、电喷雾质谱、EPR 光谱、衰减全反射红外光谱、UV-Vis 光谱、循环伏安法和元素分析进行​​表征。EPR 光谱与各向异性 Cu(II) 信号一致，在低场区域 (g||) 中有四个超精细分裂，g 值与四氯铜酸盐的存在一致。各种电子跃迁在配合物的 UV-Vis 光谱中是显而易见的，并且起源于含铜的阳离子和阴离子。密度泛函计算支持 SNS 结合的性质，允许分配存在于

  DOI：

  10.1080/00958972.2014.883070
• 作为产物：
  描述：

  在 sodium acetate 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 乙腈 为溶剂， 反应 168.5h， 以46%的产率得到2,6-bis{[N-butyl-N′-methylene]triazole-2-thione}pyridine
  参考文献：
  名称：

  Syntheses, characterization, density functional theory calculations, and activity of tridentate SNS zinc pincer complexes based on bis-imidazole or bis-triazole precursors

  摘要：

  A series of tridentate pincer ligands, each possessing two sulfur-and one nitrogen-donor functionalities (SNS), based on bis-imidazole or bis-triazole salts were metallated with ZnCl2 to give new tridentate SNS pincer zinc(II) complexes [(SNS)ZnCl](+). The zinc complexes serve as models for the zinc active site in liver alcohol dehydrogenase (LADH) and were characterized with single crystal X-ray diffraction, H-1, C-13, and HSQC NMR spectroscopies, electrospray mass spectrometry, and elemental analysis. The zinc complexes feature SNS donor atoms and pseudotetrahedral geometry about the zinc center, as is seen for liver alcohol dehydrogenase. The bond lengths and bond angles of the zinc complexes correlate well to those in horse LADH. The SNS ligand precursors were characterized with H-1, C-13, and HSQC NMR spectroscopies, elemental analysis, and cyclic voltammetry, and were found to be redox active. Gaussian calculations were performed and agree with the experimentally observed oxidation potentials for the pincer ligand precursors. The zinc complexes were screened for the reduction of electron-poor aldehydes in the presence of a hydrogen donor, 1-benzyl-1,4-dihydronicotinamide (BNAH), and it was determined that they enhance the reduction of electron-poor aldehydes. The SNS zinc pincer complexes with bis-triazole ligand precursors exhibit higher activity for the reduction of 4-nitrobenzaldehyde than do SNS zinc pincer complexes with bis-imidazole ligand precursors. Quantitative stoichiometric conversion was seen for the reduction of pyridine-2-carboxaldehyde via SNS zinc pincer complexes with either bis-imidazole or bis-triazole ligand precursors. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.047

文献信息

• Miecznikowski, John R.; Lo, Wayne; Lynn, Matthew A., Inorganica Chimica Acta, 2012, vol. 387, p. 25 - 36
  作者：Miecznikowski, John R.、Lo, Wayne、Lynn, Matthew A.、Jain, Swapan、Keilich, Lauren C.、et al.

  DOI：——

  日期：——
• Syntheses, characterization, density functional theory calculations, and activity of tridentate SNS zinc pincer complexes based on bis-imidazole or bis-triazole precursors
  作者：John R. Miecznikowski、Wayne Lo、Matthew A. Lynn、Swapan Jain、Lauren C. Keilich、Nathan F. Kloczko、Brianne E. O’Loughlin、Amanda P. DiMarzio、Kathleen M. Foley、George P. Lisi、Daniel J. Kwiecien、Elizabeth E. Butrick、Erin Powers、Raed Al-Abbasee

  DOI：10.1016/j.ica.2011.12.047

  日期：2012.5

  A series of tridentate pincer ligands, each possessing two sulfur-and one nitrogen-donor functionalities (SNS), based on bis-imidazole or bis-triazole salts were metallated with ZnCl2 to give new tridentate SNS pincer zinc(II) complexes [(SNS)ZnCl](+). The zinc complexes serve as models for the zinc active site in liver alcohol dehydrogenase (LADH) and were characterized with single crystal X-ray diffraction, H-1, C-13, and HSQC NMR spectroscopies, electrospray mass spectrometry, and elemental analysis. The zinc complexes feature SNS donor atoms and pseudotetrahedral geometry about the zinc center, as is seen for liver alcohol dehydrogenase. The bond lengths and bond angles of the zinc complexes correlate well to those in horse LADH. The SNS ligand precursors were characterized with H-1, C-13, and HSQC NMR spectroscopies, elemental analysis, and cyclic voltammetry, and were found to be redox active. Gaussian calculations were performed and agree with the experimentally observed oxidation potentials for the pincer ligand precursors. The zinc complexes were screened for the reduction of electron-poor aldehydes in the presence of a hydrogen donor, 1-benzyl-1,4-dihydronicotinamide (BNAH), and it was determined that they enhance the reduction of electron-poor aldehydes. The SNS zinc pincer complexes with bis-triazole ligand precursors exhibit higher activity for the reduction of 4-nitrobenzaldehyde than do SNS zinc pincer complexes with bis-imidazole ligand precursors. Quantitative stoichiometric conversion was seen for the reduction of pyridine-2-carboxaldehyde via SNS zinc pincer complexes with either bis-imidazole or bis-triazole ligand precursors. (C) 2011 Elsevier B. V. All rights reserved.
• Synthesis, characterization, and computational study of three-coordinate SNS-copper(I) complexes based on bis-thione precursors
  作者：John R. Miecznikowski、Matthew A. Lynn、Jerry P. Jasinski、Eric Reinheimer、Daniel W. Bak、Mekhala Pati、Elizabeth E. Butrick、Anne Elise R. Drozdoski、Kerry A. Archer、Christine E. Villa、Elise G. Lemons、Erin Powers、Margaret Siu、Camile D. Gomes、Kaitlyn N. Morio

  DOI：10.1080/00958972.2014.883070

  日期：2014.1.2

  A series of tridentate pincer ligands, each possessing two sulfur and one nitrogen donor (SNS), based on bis-imidazolyl or bis-triazolyl salts were metallated with CuCl2 to give new tridentate SNS pincer copper(I) complexes [(SNS)Cu]+. These orange complexes exhibit a three-coordinate pseudo-trigonal-planar geometry in copper. During the formation of these copper(I) complexes, disproportionation is

  一系列基于双咪唑基或双三唑基盐的三齿钳状配体（每个配体具有两个硫和一个氮供体（SNS））用 CuCl2 金属化，得到新的三齿 SNS 钳状铜（I）配合物 [(SNS)Cu] +。这些橙色配合物在铜中表现出三坐标伪三角平面几何形状。在这些铜 (I) 络合物的形成过程中，随着铜 (II) 盐前体转化为 Cu(I) [(SNS)Cu]+ 阳离子和 [CuCl4]2- 抗衡阴离子，观察到歧化。[(SNS)Cu]+ 配合物通过单晶 X 射线衍射、电喷雾质谱、EPR 光谱、衰减全反射红外光谱、UV-Vis 光谱、循环伏安法和元素分析进行​​表征。EPR 光谱与各向异性 Cu(II) 信号一致，在低场区域 (g||) 中有四个超精细分裂，g 值与四氯铜酸盐的存在一致。各种电子跃迁在配合物的 UV-Vis 光谱中是显而易见的，并且起源于含铜的阳离子和阴离子。密度泛函计算支持 SNS 结合的性质，允许分配存在于