(1,3-dioxolan-2-yl)methylbispyridin-2-ylmethylamine | 1006028-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1,3-dioxolan-2-yl)methylbispyridin-2-ylmethylamine
• 英文别名: 1-(1,3-dioxolan-2-yl)-N,N-bis(pyridin-2-ylmethyl)methanamine
• CAS: 1006028-90-5
• 化学式: C₁₆H₁₉N₃O₂
• 分子量: 285.346
• InChiKey: DIMQKIIRBVUOMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1,3-dioxolan-2-yl)methylbispyridin-2-ylmethylamine 在 盐酸 作用下， 反应 72.0h， 以119.1 mg的产率得到4-hydroxy-2-pyridin-2-ylmethyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ylium chloride hydrochloride
  参考文献：
  名称：

  A Reversible pH-Dependent Intramolecular Pyridine−Aldehyde Cyclization

  摘要：

  [GRAPHICS]A dipicolylamine (DPA) attached to an aldehyde moiety cyclizes to form a pyridinium-fused heterocycle. This intramolecular reaction between the pyridine and aldehyde moieties is reversible, and the position of the equilibrium is controlled by pH. The fused-ring heterocycle is stabilized under acidic conditions, whereas the ring-opened form is the major species under basic conditions. The ring-closed form can be utilized as a masked aldehyde precursor to access a variety of functional metal chelators containing the DPA unit.

  DOI：

  10.1021/jo702394v
• 作为产物：
  描述：

  2-(溴甲基)吡啶氢溴酸盐 、 2-(氨甲基)-1,3-二氧戊环 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以60.9%的产率得到(1,3-dioxolan-2-yl)methylbispyridin-2-ylmethylamine
  参考文献：
  名称：

  A Reversible pH-Dependent Intramolecular Pyridine−Aldehyde Cyclization

  摘要：

  [GRAPHICS]A dipicolylamine (DPA) attached to an aldehyde moiety cyclizes to form a pyridinium-fused heterocycle. This intramolecular reaction between the pyridine and aldehyde moieties is reversible, and the position of the equilibrium is controlled by pH. The fused-ring heterocycle is stabilized under acidic conditions, whereas the ring-opened form is the major species under basic conditions. The ring-closed form can be utilized as a masked aldehyde precursor to access a variety of functional metal chelators containing the DPA unit.

  DOI：

  10.1021/jo702394v