7-(10-aza-1,4-dioxa-7,13-dithiacyclopentadec-10-yl)-1-methyl-3H-phenoxazin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-(10-aza-1,4-dioxa-7,13-dithiacyclopentadec-10-yl)-1-methyl-3H-phenoxazin-3-one
• 英文别名: 7-(1,4-Dioxa-7,13-dithia-10-azacyclopentadec-10-yl)-1-methylphenoxazin-3-one；7-(1,4-dioxa-7,13-dithia-10-azacyclopentadec-10-yl)-1-methylphenoxazin-3-one
• 化学式: C₂₃H₂₈N₂O₄S₂
• 分子量: 460.618
• InChiKey: AKTMGXXYRLUUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N,N-二羟乙基苯胺 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成 7-(10-aza-1,4-dioxa-7,13-dithiacyclopentadec-10-yl)-1-methyl-3H-phenoxazin-3-one
  参考文献：
  名称：

  Coupling Selectivity with Sensitivity in an Integrated Chemosensor Framework:  Design of a Hg²⁺-Responsive Probe, Operating above 500 nm

  摘要：

  For the highly selective and sensitive sensing of Hg2+ in water, a new design concept was realized where the selectivity of the probe's binding site is amplified by electronic properties of the chromophore. The molecular architecture of this phenoxazinone-type sensor molecule combines two potential coordination sites via an amino-keto conjugative backbone. These structural prerequisites allow only the most preferred mercuric ion to bind to the dithia dioxa monoaza crown unit, while other heavy, transition, and main group metal ions as well as protons are trapped at the keto group, inducing opposite spectral effects due to interaction with either the donor (Hg2+) or the acceptor group (other cations) of the probe. Besides these advantageous features, the probe operates well within the visible range of the spectrum and displays rather intense molar absorptivities as well as fluorescence quantum yields.

  DOI：

  10.1021/ja0290779