bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine | 1261353-36-9

• 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: bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine
• 英文别名: N,N-bis[(3-bromo-1H-indol-2-yl)methyl]-1-pyridin-2-ylmethanamine
• CAS: 1261353-36-9
• 化学式: C₂₄H₂₀Br₂N₄
• 分子量: 524.258
• InChiKey: PXMGGBWIGZCVRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  bis(3-bromo-1-methoxycarbonylindol-2-ylmethyl)(2-pyridylmethyl)amine 在 potassium hydroxide 、 肼 作用下， 以 甲醇 为溶剂， 以48.4%的产率得到bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine
  参考文献：
  名称：

  Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor

  摘要：

  A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and H-1 NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl- to form a 1:1 adduct (K-a = 1042+/-21 in CD3CN). Among alkali metal ions, Li+ and Na+ showed the strongest binding in the formation of a 1.M+ complex. The simultaneous binding of Cl- and Li+ to 1 was confirmed by H-1 NMR titration of a 1:1 mixture of 1 and Cl- with LiPF6 in 83:17 viv mixture of CDCl3 and DMSO-d(6). DFT-optimized structures of 1.Cl-, 1.Li+, and 1.Lr+.Cl- are consistent with the chemical shift changes observed in H-1 NMR studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.012

文献信息

• Anion and cation binding by a new indole/pyridine/amine-based ion-pair receptor
  作者：Kristin N. Skala、Katelyn G. Perkins、Amna Ali、Robert Kutlik、Addie M. Summitt、Satyanarayana Swamy-Mruthinti、Farooq A. Khan、Megumi Fujita

  DOI：10.1016/j.tetlet.2010.10.012

  日期：2010.12

  A new ion-pair receptor bis(3-bromoindol-2-ylmethyl)(2-pyridylmethyl)amine (1) was synthesized and studied for its anion and cation binding behavior using ESI-MS and H-1 NMR spectroscopy. Among halides, 1 exhibits the strongest binding with Cl- to form a 1:1 adduct (K-a = 1042+/-21 in CD3CN). Among alkali metal ions, Li+ and Na+ showed the strongest binding in the formation of a 1.M+ complex. The simultaneous binding of Cl- and Li+ to 1 was confirmed by H-1 NMR titration of a 1:1 mixture of 1 and Cl- with LiPF6 in 83:17 viv mixture of CDCl3 and DMSO-d(6). DFT-optimized structures of 1.Cl-, 1.Li+, and 1.Lr+.Cl- are consistent with the chemical shift changes observed in H-1 NMR studies. (C) 2010 Elsevier Ltd. All rights reserved.