1,6-dihydro-6-imino-1,7-dimethyl-3-((E)-3-methylbuta-1,3-dienyl)-3H-purin-2(7H)-one | 1149670-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,6-dihydro-6-imino-1,7-dimethyl-3-((E)-3-methylbuta-1,3-dienyl)-3H-purin-2(7H)-one
• 英文别名: dioicine；6-imino-1,7-dimethyl-3-[(1E)-3-methylbuta-1,3-dienyl]purin-2-one
• CAS: 1149670-76-7
• 化学式: C₁₂H₁₅N₅O
• 分子量: 245.284
• InChiKey: MAAUOEYBVFQDIJ-CCXDTSSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6-dihydro-6-imino-1,7-dimethyl-3-((E)-3-methylbuta-1,3-dienyl)-3H-purin-2(7H)-one 在 氘代盐酸 作用下， 以 water-d2 为溶剂， 生成
  参考文献：
  名称：

  Dioicine: A Novel Prenylated Purine Alkaloid from Gymnocladus dioicus

  摘要：

  The Kentucky coffeetree, Gymnocladus dioicus (L., K. Koch) is a leguminous tree reputed to be toxic to livestock and to contain the toxic nicotinic acetylcholine receptor agonist cytisine. Analysis of extracts of various tree parts by gas chromatography-mass spectrometry failed to reveal the presence of cytisine. Neither [H-3]-epibatidine binding in rat cerebral cortex nor functional fluorescence assays in cultured cells expressing nicotinic receptor subunits indicated significant activity. However, a novel purine alkaloid, 3-((E)-3-methylbuta-1,3-dienyl)-1,7-dimethylisoguanine, which we have named dioicine, was identified as the major lipophilic alkaloid in the methanolic extract from leaves and seeds. Dioicine and its hydrolysis products are likely to be responsible for the historical use of the tree's seeds as a coffee substitute. Herein we describe the isolation, structure elucidation and preliminary biological characterization of dioicine.

  DOI：

  10.3987/com-08-s(d)19