N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine | 1263199-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine
• 英文别名: N'-benzyl-N'-quinol-2-ylmethyl-N,N-dimethylethylenediamine；N'-benzyl-N'-(isoquinolin-3-ylmethyl)-N,N-dimethylethane-1,2-diamine
• CAS: 1263199-46-7
• 化学式: C₂₁H₂₅N₃
• 分子量: 319.45
• InChiKey: BWFSCOWYECLFME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 copper(II) choride dihydrate 、 N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine 以 甲醇 为溶剂， 以65%的产率得到Cu(N'-benzyl-N'-quinol-2-ylmethyl-N,N-dimethylethylenediamine)Cl2
  参考文献：
  名称：

  Olefin aziridination by copper(II) complexes: Effect of redox potential on catalytic activity

  摘要：

  A series of new copper(II) complexes of four sterically hindering linear tridentate 3N ligands N'-ethyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L1), N'-benzyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L2), N'-benzyl-N'-(6-methylpyrid-2-yl-methyl)-N,N-dimethylethylenediamine (L3) and N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine (L4) have been isolated and examined as catalysts for olefin aziridination. The complexes [Cu(L1)Cl-2]center dot CH3OH 1, [Cu(L2)Cl-2]center dot CH3OH 2, [Cu(L3)Cl-2]center dot 0.5 H2O 3 and [Cu(L4)Cl-2] 4 have been structurally characterized by X-ray crystallography. In all of them copper(II) adopts a slightly distorted square pyramidal geometry as inferred from the values of trigonality index (tau) for them (tau: 1, 0.02; 2, 0.01; 3, 0.07; 4, 0.01). Electronic and EPR spectral studies reveal that the complexes retain square-based geometry in solution also. The complexes undergo quasireversible Cu(II)/Cu(I) redox behavior (E-1/2, -0.272 - -0.454 V) in acetonitrile solution. The ability of the complexes to mediate nitrene transfer from PhINTs and chloramine-T trihydrate to olefins to form N-tosylaziridines has been studied. The complexes 3 and 4 catalyze the aziridination of styrene very slowly yielding above 80% of the desired product. They also catalyze the aziridination of the less reactive olefins like cyclooctene and n-hexene but with lower yields (30-50%). In contrast to these two complexes, 1 and 2 fail to catalyze the aziridination of olefins in the presence of both the nitrene sources. All these observations have been rationalized based on the Cu(II)/Cu(I) redox potentials of the catalysts. (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2010.08.051
• 作为产物：
  描述：

  喹啉-2-甲醛 、 N'-苯甲基-N,N-二甲基乙二胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 42.0h， 以40%的产率得到N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine
  参考文献：
  名称：

  Olefin aziridination by copper(II) complexes: Effect of redox potential on catalytic activity

  摘要：

  A series of new copper(II) complexes of four sterically hindering linear tridentate 3N ligands N'-ethyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L1), N'-benzyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L2), N'-benzyl-N'-(6-methylpyrid-2-yl-methyl)-N,N-dimethylethylenediamine (L3) and N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine (L4) have been isolated and examined as catalysts for olefin aziridination. The complexes [Cu(L1)Cl-2]center dot CH3OH 1, [Cu(L2)Cl-2]center dot CH3OH 2, [Cu(L3)Cl-2]center dot 0.5 H2O 3 and [Cu(L4)Cl-2] 4 have been structurally characterized by X-ray crystallography. In all of them copper(II) adopts a slightly distorted square pyramidal geometry as inferred from the values of trigonality index (tau) for them (tau: 1, 0.02; 2, 0.01; 3, 0.07; 4, 0.01). Electronic and EPR spectral studies reveal that the complexes retain square-based geometry in solution also. The complexes undergo quasireversible Cu(II)/Cu(I) redox behavior (E-1/2, -0.272 - -0.454 V) in acetonitrile solution. The ability of the complexes to mediate nitrene transfer from PhINTs and chloramine-T trihydrate to olefins to form N-tosylaziridines has been studied. The complexes 3 and 4 catalyze the aziridination of styrene very slowly yielding above 80% of the desired product. They also catalyze the aziridination of the less reactive olefins like cyclooctene and n-hexene but with lower yields (30-50%). In contrast to these two complexes, 1 and 2 fail to catalyze the aziridination of olefins in the presence of both the nitrene sources. All these observations have been rationalized based on the Cu(II)/Cu(I) redox potentials of the catalysts. (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2010.08.051