N-[6-[[bis(2-pyridin-2-ylethyl)amino]methyl]-4-oxo-3H-pteridin-2-yl]-2,2-dimethylpropanamide | 139242-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: N-[6-[[bis(2-pyridin-2-ylethyl)amino]methyl]-4-oxo-3H-pteridin-2-yl]-2,2-dimethylpropanamide
• CAS: 139242-64-1
• 化学式: C₂₆H₃₀N₈O₂
• 分子量: 486.577
• InChiKey: JCIFEUUCDDTYTM-UHFFFAOYSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrakis(actonitrile)copper(I) hexafluorophosphate 、 N-[6-[[bis(2-pyridin-2-ylethyl)amino]methyl]-4-oxo-3H-pteridin-2-yl]-2,2-dimethylpropanamide 以 二氯甲烷 为溶剂， 生成 N-[6-[[bis(2-pyridin-2-ylethyl)amino]methyl]-4-oxo-1H-pteridin-2-yl]-2,2-dimethylpropanamide;copper(1+);hexafluorophosphate
  参考文献：
  名称：

  Nasir, M. Sarwar; Karlin, Kenneth D.; Qin, Chen, Journal of the American Chemical Society, 1992, vol. 114, p. 2264 - 2265

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-6-甲基-4(3H)-蝶啶酮 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 生成 N-[6-[[bis(2-pyridin-2-ylethyl)amino]methyl]-4-oxo-3H-pteridin-2-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Copper(I) and copper(II) complexes of new chelating pterins

  摘要：

  DOI：

  10.1021/ja00032a054

文献信息

• Copper Ion Complexes with Derivatized Chelating Pterin Ligands
  作者：Dong-Heon Lee、Narasimha N. Murthy、Yin Lin、N. Sarwar Nasir、Kenneth D. Karlin

  DOI：10.1021/ic970810k

  日期：1997.12.1

  Pterin-copper ion interactions are of interest for possible modeling of enzyme active site chemistry or in coupling reactions of a redox-active metal ion with a redox-active ligand cofactor, Here, we describe the synthesis of derivatized chelating pterins, provided with enhanced organic solubility by introduction of a pivalolyl group the pterin C2 position and supplied with a good copper ion chelator, through reaction of the 6-(bromomethyl)pterin with a 2-(2-(methylamino)ethyl)pyridine (to give L') or bis(2-pyrid-2-ylethyl)amine (to give L). Copper(I) and copper(II) complexes have been synthesized and characterized. The X-ray structure of [L'Cu(CI)(CH3CN)](PF6) (3-PF6) is described [space group P2(1)/c; a = 10.606(3) Angstrom, b = 21.683(3) Angstrom, c = 12.188(3) Angstrom; beta = 96.67(2)degrees; Z = 3; V = 2784(1) Angstrom(3)] and compared with the previously reported structure of [LCu(Cl)](PF6)(NaPF6) (1-PF6 . NaPF6). In 3-PF6, the Cu(II) is pentacoordinate, including equatorial ligation to the pterin N5 atom, achieving one of the goals of the ligand design. Unlike other pterin-Cu(II) structures, neither 1-PF6 . NaPF6 nor 3-PF6 binds to the pterin carbonyl oxygen atom (off pterin C4). Other solution spectroscopic data (e.g., IR, UV-vis, EPR) and a magnetic moment of 1.91 mu(B) are provided and are consistent with the solid-state structure observed. Copper(I) complexes [L'Cu-I](PF6) (5-PF6) and [L'Cu-I](PF6). 0.25CH(2)Cl(2) (6-PF6 . 0.25CH(2)Cl(2)) have been generated and characterized. Observed coordination-induced H-1 NMR chemical shifts in 6-PF6 . 0.25CH(2)Cl(2)) are consistent with binding through the pterin pyrazine N5 donor; a W-vis feature at 466 nm (sh, epsilon = 1200) is considered a MLCT transition. A cyclic voltammogram of 6-PF6 . 0.25CH(2)Cl(2) (DMF solvent) reveals reversible redox process with E-1/2 = 286 mV (E-1/2 = 546 mV for ferrocene/ferrocenium; vs Ag/AgCl). [L'Cu-II(CH3CN)](CF3SO3)(2) (4-(CF3SO3)(2)) exhibits the identical cyclic voltammogram, indicating common solution structures. The analogue complex [(MeL)Cu-I(CH3CN)](ClO4) (7-ClO4) (Met = (2-(2-pyridyl)ethyl) (2-pyridylmethyl)methylamine) displays a more negative redox potential, E-1/2 = 24 mV, indicating that the pterin pyrazine ring has an electron-withdrawing effect, which may explain the lack of O-2 reactivity of copper(I) complexes of L and L'.