3-Butoxy-4-[1-methyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1H-quinolin-(2E)-ylidenemethyl]-cyclobut-3-ene-1,2-dione | 874949-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-Butoxy-4-[1-methyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1H-quinolin-(2E)-ylidenemethyl]-cyclobut-3-ene-1,2-dione
• CAS: 874949-70-9
• 化学式: C₂₅H₂₉NO₉
• 分子量: 487.507
• InChiKey: ZUFCZUHIFUFYPY-CZPMXYLCSA-N

物化性质

• 沸点：
  725.3±70.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  145.99
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-Butoxy-4-[1-methyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1H-quinolin-(2E)-ylidenemethyl]-cyclobut-3-ene-1,2-dione 、 6-iodo-N-methyl-2-quinaldinium iodide 在 喹啉 作用下， 以 正丁醇 、 苯 为溶剂， 反应 12.0h， 以70%的产率得到4-[(6-iodo-1-methylquinolin-1-ium-2-yl)methylidene]-2-[[1-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyquinolin-2-ylidene]methyl]-3-oxocyclobuten-1-olate
  参考文献：
  名称：

  Synthesis of New Cholesterol- and Sugar-Anchored Squaraine Dyes:  Further Evidence of How Electronic Factors Influence Dye Formation

  摘要：

  Synthesis of new quinaldine-based squaraine dyes linked to cellular recognition elements that exhibit near-infrared absorption (> 740 nm) are described. Both product analysis and theoretical calculations substantiate the interesting electronic effects of various substituents in the dye formation reaction. These results are useful in the synthesis of symmetrical and unsymmetrical squaraine dyes that can have potential biological and photodynamic therapeutical applications.

  DOI：

  10.1021/ol052639j
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl bromide 在 喹啉 、 sodium hydroxide 、 四丁基溴化铵 、 sodium methylate 作用下， 以 甲醇 、 氯仿 、 乙腈 、 苯 为溶剂， 反应 47.0h， 生成 3-Butoxy-4-[1-methyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1H-quinolin-(2E)-ylidenemethyl]-cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis of New Cholesterol- and Sugar-Anchored Squaraine Dyes:  Further Evidence of How Electronic Factors Influence Dye Formation

  摘要：

  Synthesis of new quinaldine-based squaraine dyes linked to cellular recognition elements that exhibit near-infrared absorption (> 740 nm) are described. Both product analysis and theoretical calculations substantiate the interesting electronic effects of various substituents in the dye formation reaction. These results are useful in the synthesis of symmetrical and unsymmetrical squaraine dyes that can have potential biological and photodynamic therapeutical applications.

  DOI：

  10.1021/ol052639j