2-amino-6-(hydroxymethyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one;hydrochloride

• 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: 2-amino-6-(hydroxymethyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one;hydrochloride
• 化学式: C₇H₁₁N₅O₂*2ClH
• 分子量: 270.119
• InChiKey: CHXHYPIZJNVGPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.03
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  112
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 2-amino-6-(hydroxymethyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one;hydrochloride 以 甲醇 、 氯仿 为溶剂， 以56%的产率得到
  参考文献：
  名称：

  Tetrahydropterin Reactions of Dioxo-Molybdenum(6+) Complexes: Does Redox Occur?

  摘要：

  This report describes out continued investigation of reactions between tetrahydropterins and dioxomolybdenum complexes. We report the results of structural, reactivity, and theoretical experiments that indicate these reduced molybdenum-pterin complexes are better described as Mo(6+)-H(4)pterin rather than Mo(4+)-H(2)pterin as previously assigned. Both Mulliken charges calculated using the extended Huckel molecular orbital method and the bond valence sum method predict a formal molybdenum oxidation state midway between 5+ and 6+. The complexes Mo2O4Cl2(tetrahydro-6,7-dimethylpterin)(2), MoOCl3(tetrahydro-6,7-dimethylpterin), and MoOCl2(tetrahydro-6-(hydroxymethyl)pterin)(diethyldithiocarbaate) have been characterized by H-1 NMR, IR, UV/vis, and conductivity measurements. The X-ray crystal structure is reported for Mo2O4Cl2(tetrahydro-6,7-dimethylpterin)(2) . 4DMF. Inner coordination sphere bond distances indicate substantial electron density is donated from the pterin N(5) to Mo. These complexes undergo solvation and ligand substitution reactions. It is shown that solvation is associated with acid-base reactions at the tetrahydropterin ligands. The molybdenum-tetrahydropterin complexes show a variety of reactivities toward the oxidants O-2, 2,6-dichloroindophenol, and dimethyl sulfoxide. This study shows that tetrahydropterin has a high affinity to chelate Mo(6+) if one of the two oxo ligands is removed and that coordination to molybdenum stabilizes tetrahydropterins toward oxidation. Results from this study also suggest that dioxo-Mo(VI) coordination to tetrahydropterin is unlikely.

  DOI：

  10.1021/ja00126a020

文献信息

• Tetrahydropterin Reactions of Dioxo-Molybdenum(6+) Complexes: Does Redox Occur?
  作者：Sharon J. Nieter Burgmayer、Michelle R. Arkin、Laura Bostick、Sara Dempster、Kristin M. Everett、Heather L. Layton、Kateri E. Paul、Cory Rogge、Arnold L. Rheingold

  DOI：10.1021/ja00126a020

  日期：1995.5

  This report describes out continued investigation of reactions between tetrahydropterins and dioxomolybdenum complexes. We report the results of structural, reactivity, and theoretical experiments that indicate these reduced molybdenum-pterin complexes are better described as Mo(6+)-H(4)pterin rather than Mo(4+)-H(2)pterin as previously assigned. Both Mulliken charges calculated using the extended Huckel molecular orbital method and the bond valence sum method predict a formal molybdenum oxidation state midway between 5+ and 6+. The complexes Mo2O4Cl2(tetrahydro-6,7-dimethylpterin)(2), MoOCl3(tetrahydro-6,7-dimethylpterin), and MoOCl2(tetrahydro-6-(hydroxymethyl)pterin)(diethyldithiocarbaate) have been characterized by H-1 NMR, IR, UV/vis, and conductivity measurements. The X-ray crystal structure is reported for Mo2O4Cl2(tetrahydro-6,7-dimethylpterin)(2) . 4DMF. Inner coordination sphere bond distances indicate substantial electron density is donated from the pterin N(5) to Mo. These complexes undergo solvation and ligand substitution reactions. It is shown that solvation is associated with acid-base reactions at the tetrahydropterin ligands. The molybdenum-tetrahydropterin complexes show a variety of reactivities toward the oxidants O-2, 2,6-dichloroindophenol, and dimethyl sulfoxide. This study shows that tetrahydropterin has a high affinity to chelate Mo(6+) if one of the two oxo ligands is removed and that coordination to molybdenum stabilizes tetrahydropterins toward oxidation. Results from this study also suggest that dioxo-Mo(VI) coordination to tetrahydropterin is unlikely.