2-phenyl-N-((1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)diazenecarboxamide | 1224434-20-1

• 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-phenyl-N-((1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)diazenecarboxamide
• 英文别名: 1-Phenylimino-3-[[1-(pyridin-2-ylmethyl)triazol-4-yl]methyl]urea；1-phenylimino-3-[[1-(pyridin-2-ylmethyl)triazol-4-yl]methyl]urea
• CAS: 1224434-20-1
• 化学式: C₁₆H₁₅N₇O
• 分子量: 321.341
• InChiKey: MBZDHGGHJBHYOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(dimethylsulfoxide)platinum(II) 、 2-phenyl-N-((1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)diazenecarboxamide 以 乙腈 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  Synthesis and Characterization of Platinum(II) Complexes with a Diazenecarboxamide‐Appended Picolyl‐Triazole Ligand

  摘要：

  AbstractThe coordination of the diazenecarboxamides, which were functionalized with the 1‐(2‐picolyl)‐1H‐1,2,3‐triazole moiety 1, to platinum(II) were studied, where K2[PtCl4] and cis‐[PtCl2(DMSO)2] were used as the platinum sources. The picolyl‐triazole (pictri) binding unit enabled chelation to the metal centre through the 1,2,3‐triazole N2 and the pyridyl nitrogen atoms under mild reaction conditions. When cis‐[PtCl2(DMSO)2] was used, with CH2Cl2 or CH3CN as the reaction solvents, the pure, stable diamminedichloridoplatinum(II) complexes 2 were isolated by filtration in 39 to 83 % yield. The products were structurally characterized in solution by 1H, 13C and 195Pt NMR spectroscopy. The 195Pt NMR chemical shifts for 2 appear in the region of –2203 to –2207 ppm. The structure of complex 2a was confirmed by single‐crystal X‐ray crystallography. The formation of the platinum complexes 2 was monitored using NMR spectroscopy. The complexation with cis‐[PtCl2(DMSO)2] in [D7]dmf proceeded through several intermediates, as indicated by the 195Pt NMR spectra with resonances in the range of –3055 to –2907 ppm. Similarly, the reaction of cis‐[PtCl2(DMSO)2] with diazenecarboxamide, which was functionalized with the nonchelating 1‐(2‐aminoethyl)‐1,2,3‐triazole derivative, was examined by NMR spectroscopy.

  DOI：

  10.1002/ejic.201001051
• 作为产物：
  描述：

  2-(叠氮基甲基)吡啶 、 2-phenyl-N-(prop-2-ynyl)diazenecarboxamide 在 copper(ll) sulfate pentahydrate 、 铜 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以99%的产率得到2-phenyl-N-((1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)diazenecarboxamide
  参考文献：
  名称：

  N-（丙炔基）二氮杂羧酰胺在Cu（II）存在下用于'点击'偶联及其与叠氮基烷基胺的1,3-偶极环加成反应

  摘要：

  炔丙基官能化的二氮烯1通过两种不同的方法制备，并在铜催化的叠氮化物-炔烃环加成（CuAAC）中与2-（叠氮甲基）吡啶5a和四个α-叠氮基-ω-氨基链烷烃C2-C5（5b – e）。与叠氮基烷基胺5b - e的反应通常用硫酸铜（II）在不需要还原剂的情况下通常在不超过几分钟的时间内完成，而2-（叠氮甲基）吡啶5a需要添加金属铜和更长的反应时间（2 –24小时）。研究了反应性的这种差异，并根据其对CuAAC的碱效应和邻近效应进行了研究。

  DOI：

  10.1016/j.tet.2010.02.042

文献信息

• N-(Propargyl)diazenecarboxamides for ‘click’ conjugation and their 1,3-dipolar cycloadditions with azidoalkylamines in the presence of Cu(II)
  作者：Damijana Urankar、Miha Steinbücher、Jaka Kosjek、Janez Košmrlj

  DOI：10.1016/j.tet.2010.02.042

  日期：2010.4

  Propargyl functionalized diazenes 1 were prepared by two different approaches and were examined as alkyne click components in copper-catalyzed azide–alkyne cycloadditions (CuAAC) with 2-(azidomethyl)pyridine 5a and four α-azido-ω-aminoalkanes C2–C5 (5b–e). Whereas the reactions with azidoalkylamines 5b–e reached completion with copper(II) sulfate without the need of reducing agent typically in no more

  炔丙基官能化的二氮烯1通过两种不同的方法制备，并在铜催化的叠氮化物-炔烃环加成（CuAAC）中与2-（叠氮甲基）吡啶5a和四个α-叠氮基-ω-氨基链烷烃C2-C5（5b – e）。与叠氮基烷基胺5b - e的反应通常用硫酸铜（II）在不需要还原剂的情况下通常在不超过几分钟的时间内完成，而2-（叠氮甲基）吡啶5a需要添加金属铜和更长的反应时间（2 –24小时）。研究了反应性的这种差异，并根据其对CuAAC的碱效应和邻近效应进行了研究。
• Synthesis and Characterization of Platinum(II) Complexes with a Diazenecarboxamide‐Appended Picolyl‐Triazole Ligand
  作者：Damijana Urankar、Andrej Pevec、Janez Košmrlj

  DOI：10.1002/ejic.201001051

  日期：2011.4

  AbstractThe coordination of the diazenecarboxamides, which were functionalized with the 1‐(2‐picolyl)‐1H‐1,2,3‐triazole moiety 1, to platinum(II) were studied, where K2[PtCl4] and cis‐[PtCl2(DMSO)2] were used as the platinum sources. The picolyl‐triazole (pictri) binding unit enabled chelation to the metal centre through the 1,2,3‐triazole N2 and the pyridyl nitrogen atoms under mild reaction conditions. When cis‐[PtCl2(DMSO)2] was used, with CH2Cl2 or CH3CN as the reaction solvents, the pure, stable diamminedichloridoplatinum(II) complexes 2 were isolated by filtration in 39 to 83 % yield. The products were structurally characterized in solution by 1H, 13C and 195Pt NMR spectroscopy. The 195Pt NMR chemical shifts for 2 appear in the region of –2203 to –2207 ppm. The structure of complex 2a was confirmed by single‐crystal X‐ray crystallography. The formation of the platinum complexes 2 was monitored using NMR spectroscopy. The complexation with cis‐[PtCl2(DMSO)2] in [D7]dmf proceeded through several intermediates, as indicated by the 195Pt NMR spectra with resonances in the range of –3055 to –2907 ppm. Similarly, the reaction of cis‐[PtCl2(DMSO)2] with diazenecarboxamide, which was functionalized with the nonchelating 1‐(2‐aminoethyl)‐1,2,3‐triazole derivative, was examined by NMR spectroscopy.