dimethyl 5-(2,5,8,11-tetraoxatridecan-13-yloxy)isophthalate | 935279-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 5-(2,5,8,11-tetraoxatridecan-13-yloxy)isophthalate
• 英文别名: Dimethyl 5-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]benzene-1,3-dicarboxylate
• CAS: 935279-99-5
• 化学式: C₁₉H₂₈O₉
• 分子量: 400.426
• InChiKey: USUNXGQIXQHXOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 5-(2,5,8,11-tetraoxatridecan-13-yloxy)isophthalate 在 sodium hydroxide 、 硫酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.5h， 生成 3-(2,5,8,11-tetraoxatridecan-13-yloxy)-5-(methoxycarbonyl)benzoic acid
  参考文献：
  名称：

  Phenanthroline-Derived Ratiometric Chemosensor for Ureas

  摘要：

  The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 are reported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(1H)-one, imidazolidin-2-one, and selected uronium salts were assessed by three-dimensional excitation-emission spectroscopy, UV-vis absorbance, and fluorescence titrations. Chemosensor 7 was found to be capable of distinguishing between neutral ureas and their salts, by producing a different optical response for each type of compounds. The complexation of urea by 7 was also studied by selective-NOE H-1 NMR, C-13 NMR (using C-13-labeled guest), and MALDI-TOF mass spectrometry. In addition, we performed DFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(1H)-one. Development of chemosensor 7-type compounds in conjunction with differential excitation-emission spectroscopy represents an important step toward the development of novel tools for ureas and their salts analysis.

  DOI：

  10.1021/jo062130h
• 作为产物：
  描述：

  5-羟基间苯二甲酸二甲酯 、 2,5,8,11-四氧杂十三烷-13-基4-甲基苯磺酸酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以98%的产率得到dimethyl 5-(2,5,8,11-tetraoxatridecan-13-yloxy)isophthalate
  参考文献：
  名称：

  Phenanthroline-Derived Ratiometric Chemosensor for Ureas

  摘要：

  The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 are reported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(1H)-one, imidazolidin-2-one, and selected uronium salts were assessed by three-dimensional excitation-emission spectroscopy, UV-vis absorbance, and fluorescence titrations. Chemosensor 7 was found to be capable of distinguishing between neutral ureas and their salts, by producing a different optical response for each type of compounds. The complexation of urea by 7 was also studied by selective-NOE H-1 NMR, C-13 NMR (using C-13-labeled guest), and MALDI-TOF mass spectrometry. In addition, we performed DFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(1H)-one. Development of chemosensor 7-type compounds in conjunction with differential excitation-emission spectroscopy represents an important step toward the development of novel tools for ureas and their salts analysis.

  DOI：

  10.1021/jo062130h

文献信息

• Phenanthroline-Derived Ratiometric Chemosensor for Ureas
  作者：Yoni Engel、Adi Dahan、Emily Rozenshine-Kemelmakher、Michael Gozin

  DOI：10.1021/jo062130h

  日期：2007.3.1

  The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 are reported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(1H)-one, imidazolidin-2-one, and selected uronium salts were assessed by three-dimensional excitation-emission spectroscopy, UV-vis absorbance, and fluorescence titrations. Chemosensor 7 was found to be capable of distinguishing between neutral ureas and their salts, by producing a different optical response for each type of compounds. The complexation of urea by 7 was also studied by selective-NOE H-1 NMR, C-13 NMR (using C-13-labeled guest), and MALDI-TOF mass spectrometry. In addition, we performed DFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(1H)-one. Development of chemosensor 7-type compounds in conjunction with differential excitation-emission spectroscopy represents an important step toward the development of novel tools for ureas and their salts analysis.