N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole | 481050-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole
• 英文别名: 2-[[1H-indol-3-ylmethyl(pyridin-2-ylmethyl)amino]methyl]phenol
• CAS: 481050-72-0
• 化学式: C₂₂H₂₁N₃O
• 分子量: 343.428
• InChiKey: NIMWBCGEEHLXQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  532.5±45.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole 在 (C₂H₅)3N 作用下， 以 乙腈 为溶剂， 生成 [Cu(N-2-pyridylmethyl-N-2-oxybenzyl-3-aminomethylindole)2Cu] perchlorate
  参考文献：
  名称：

  Conformational preference of the side chain aromatic ring in Cu(II) and Pd(II) complexes of 2N1O-donor ligands

  摘要：

  Synthetic, structural, and spectroscopic studies were performed on the copper(H) and palladium(II) complexes of various 2N1O-donor tripod-like ligands containing a pyridine or a dimethylamine nitrogen, a tertiary amine nitrogen, and a phenolate oxygen as donor atoms and a pendent indole ring. [Pd(impp)Cl].3H(2)O.CH3CN (impp = N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole) and two other Pd(II) complexes and a Cu(II) complex were isolated as crystals and structurally characterized by the X-ray diffraction method. The indole moiety of the Pd(II) complexes was found to be located close to the pyridine ring or the dimethylamino group and away from the phenolate moiety. H-1 NMR spectra of the Pd(II) complexes in CD3CN exhibited large upfield shifts of the pyridine and dimethylamino proton signals due to the pendent indole ring, supporting that the complexes in solution have a stacked structure similar to that found in the solid state. These findings indicated that the aromatic ring stacking interactions or CH-pi interactions exist between the indole and the pyridine rings or the methyl groups, respectively. [Cu-2(impp)(2)](ClO4)(2).H2O was revealed to have a dimeric structure with the indole moiety close to both the Cu(II) center and the pyridine ring, which suggests the possibility that the Cu(II) ion may undergo metal-aromatic ring interactions. (C) 2002 Published by Elsevier Science B.V.

  DOI：

  10.1016/s0020-1693(02)01034-4
• 作为产物：
  描述：

  3-吲哚甲醛 、 N-(2-pyridylmethyl)-2-hydroxybenzylamine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.83h， 以90%的产率得到N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole
  参考文献：
  名称：

  Efficient synthesis of new asymmetric tripodal ligands using microwave irradiation, and their crystal structures

  摘要：

  使用微波辐射描述了一种合成非对称三脚镧配体的高效方法。

  DOI：

  10.1039/c4ra07346k

文献信息

• Conformational preference of the side chain aromatic ring in Cu(II) and Pd(II) complexes of 2N1O-donor ligands
  作者：Tatsuo Yajima、Yuichi Shimazaki、Naoya Ishigami、Akira Odani、Osamu Yamauchi

  DOI：10.1016/s0020-1693(02)01034-4

  日期：2002.9

  Synthetic, structural, and spectroscopic studies were performed on the copper(H) and palladium(II) complexes of various 2N1O-donor tripod-like ligands containing a pyridine or a dimethylamine nitrogen, a tertiary amine nitrogen, and a phenolate oxygen as donor atoms and a pendent indole ring. [Pd(impp)Cl].3H(2)O.CH3CN (impp = N-2-pyridylmethyl-N-2-hydroxybenzyl-3-aminomethylindole) and two other Pd(II) complexes and a Cu(II) complex were isolated as crystals and structurally characterized by the X-ray diffraction method. The indole moiety of the Pd(II) complexes was found to be located close to the pyridine ring or the dimethylamino group and away from the phenolate moiety. H-1 NMR spectra of the Pd(II) complexes in CD3CN exhibited large upfield shifts of the pyridine and dimethylamino proton signals due to the pendent indole ring, supporting that the complexes in solution have a stacked structure similar to that found in the solid state. These findings indicated that the aromatic ring stacking interactions or CH-pi interactions exist between the indole and the pyridine rings or the methyl groups, respectively. [Cu-2(impp)(2)](ClO4)(2).H2O was revealed to have a dimeric structure with the indole moiety close to both the Cu(II) center and the pyridine ring, which suggests the possibility that the Cu(II) ion may undergo metal-aromatic ring interactions. (C) 2002 Published by Elsevier Science B.V.
• Efficient synthesis of new asymmetric tripodal ligands using microwave irradiation, and their crystal structures
  作者：Zeli Yuan、Xiaoqing Yang、Lei Wang、Jiandong Huang、Gang Wei

  DOI：10.1039/c4ra07346k

  日期：——

  An efficient method for synthesis of asymmetric tripodal ligands was described by using microwave irradiation.

  使用微波辐射描述了一种合成非对称三脚镧配体的高效方法。