2-[2-(3-Phenylmethoxynaphthalen-2-yl)oxyethoxy]ethyl 4-methylbenzenesulfonate | 776332-02-6

• 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: 2-[2-(3-Phenylmethoxynaphthalen-2-yl)oxyethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 776332-02-6
• 化学式: C₂₈H₂₈O₆S
• 分子量: 492.593
• InChiKey: LCNOADKHKGMDGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(3-Phenylmethoxynaphthalen-2-yl)oxyethoxy]ethyl 4-methylbenzenesulfonate 在 碳酸氢钠 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-[2-(2-Bromoethoxy)ethoxy]-3-[2-[2-(3-phenylmethoxynaphthalen-2-yl)oxyethoxy]ethoxy]naphthalene
  参考文献：
  名称：

  Solvophobically-Driven Oligo(ethylene glycol) Helical Foldamers. Synthesis, Characterization, and Complexation with Ethane-1,2-diaminium

  摘要：

  Oligo(ethylene glycols) la-h, which are incorporated with one to eight 2,3-naphthylene units, respectively, have been synthesized and characterized. The conformational changes of the new oligomers have been investigated in chloroform- acetonitrile binary solvents by the LTV-vis, H-1 NMR, and fluorescent spectroscopy. It has been revealed that the naphthalene units in hexamer 1f, heptamer 1g, and octamer 1h are driven by solvophobic interaction to stack in polar solvents. As a result, compact helical conformations are formed that give rise to a cavity similar to that of 18-crown-6. Shorter oligomers 1b-e exhibit weaker folding tendency. H-1 NMR studies reveal that 1f-h are able to complex ammonium or ethane-1,2-diaminium 19, but not secondary ammonium compounds. The association constants of complexes 1f(.)19, 1g(.)19, and 1h(.)19 in acetonitrile are determined to be 3.5(+/-0.4) x 10(3), 1.0(+/-0.12) x 10(4), and 2.5(+/-0.4) x 10(4) M-1, respectively, with the H-1 NMR titration method. For comparison, hexamer 22, which incorporates six 1,5-naphthylene units, is also prepared. The LTV-vis and fluorescent investigations show that 22 is also able to fold in polar solvents, but no helical structure can be produced due to mismatch of the stacking naphthalene units and consequently there is no obvious complexation between 22 with ethane-1,2-diaminium ion. The structures of the longest foldamer 1h and its complex with 19 have been studied with molecular mechanics calculations. This work represents a new approach to building folding conformations from flexible linear molecules.

  DOI：

  10.1021/jo049420n
• 作为产物：
  描述：

  3-benzyloxynaphthalen-2-ol 、 二乙二醇双对甲苯磺酸酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以81%的产率得到2-[2-(3-Phenylmethoxynaphthalen-2-yl)oxyethoxy]ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Solvophobically-Driven Oligo(ethylene glycol) Helical Foldamers. Synthesis, Characterization, and Complexation with Ethane-1,2-diaminium

  摘要：

  Oligo(ethylene glycols) la-h, which are incorporated with one to eight 2,3-naphthylene units, respectively, have been synthesized and characterized. The conformational changes of the new oligomers have been investigated in chloroform- acetonitrile binary solvents by the LTV-vis, H-1 NMR, and fluorescent spectroscopy. It has been revealed that the naphthalene units in hexamer 1f, heptamer 1g, and octamer 1h are driven by solvophobic interaction to stack in polar solvents. As a result, compact helical conformations are formed that give rise to a cavity similar to that of 18-crown-6. Shorter oligomers 1b-e exhibit weaker folding tendency. H-1 NMR studies reveal that 1f-h are able to complex ammonium or ethane-1,2-diaminium 19, but not secondary ammonium compounds. The association constants of complexes 1f(.)19, 1g(.)19, and 1h(.)19 in acetonitrile are determined to be 3.5(+/-0.4) x 10(3), 1.0(+/-0.12) x 10(4), and 2.5(+/-0.4) x 10(4) M-1, respectively, with the H-1 NMR titration method. For comparison, hexamer 22, which incorporates six 1,5-naphthylene units, is also prepared. The LTV-vis and fluorescent investigations show that 22 is also able to fold in polar solvents, but no helical structure can be produced due to mismatch of the stacking naphthalene units and consequently there is no obvious complexation between 22 with ethane-1,2-diaminium ion. The structures of the longest foldamer 1h and its complex with 19 have been studied with molecular mechanics calculations. This work represents a new approach to building folding conformations from flexible linear molecules.

  DOI：

  10.1021/jo049420n

文献信息

• Solvophobically-Driven Oligo(ethylene glycol) Helical Foldamers. Synthesis, Characterization, and Complexation with Ethane-1,2-diaminium
  作者：Jun-Li Hou、Mu-Xin Jia、Xi-Kui Jiang、Zhan-Ting Li、Guang-Ju Chen

  DOI：10.1021/jo049420n

  日期：2004.9.1

  Oligo(ethylene glycols) la-h, which are incorporated with one to eight 2,3-naphthylene units, respectively, have been synthesized and characterized. The conformational changes of the new oligomers have been investigated in chloroform- acetonitrile binary solvents by the LTV-vis, H-1 NMR, and fluorescent spectroscopy. It has been revealed that the naphthalene units in hexamer 1f, heptamer 1g, and octamer 1h are driven by solvophobic interaction to stack in polar solvents. As a result, compact helical conformations are formed that give rise to a cavity similar to that of 18-crown-6. Shorter oligomers 1b-e exhibit weaker folding tendency. H-1 NMR studies reveal that 1f-h are able to complex ammonium or ethane-1,2-diaminium 19, but not secondary ammonium compounds. The association constants of complexes 1f(.)19, 1g(.)19, and 1h(.)19 in acetonitrile are determined to be 3.5(+/-0.4) x 10(3), 1.0(+/-0.12) x 10(4), and 2.5(+/-0.4) x 10(4) M-1, respectively, with the H-1 NMR titration method. For comparison, hexamer 22, which incorporates six 1,5-naphthylene units, is also prepared. The LTV-vis and fluorescent investigations show that 22 is also able to fold in polar solvents, but no helical structure can be produced due to mismatch of the stacking naphthalene units and consequently there is no obvious complexation between 22 with ethane-1,2-diaminium ion. The structures of the longest foldamer 1h and its complex with 19 have been studied with molecular mechanics calculations. This work represents a new approach to building folding conformations from flexible linear molecules.