2,6-二乙炔基-4-(辛氧基)吡啶 | 1032413-28-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,6-二乙炔基-4-(辛氧基)吡啶
• 英文名称: 2,6-diethynyl-4-(octyloxy)pyridine
• CAS: 1032413-28-7
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: HVLICDGHDSKZPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,6-二乙炔基-4-(辛氧基)吡啶 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 2-({3-[(tert-butyldimethylsilyl)ethynyl]-2-(methoxymethoxy)-5-pentylphenyl}ethynyl)-6-{[3-(3-hydroxy-3-methyl-1-butynyl)-2-(methoxymethoxy)-5-pentylphenyl]ethynyl}-4-(octyloxy)pyridine
  参考文献：
  名称：

  吡啶-苯酚交替低聚物对氢键受体和供体的重复母题具有极高的重复母题，从而提取出天然的甘露糖优势

  摘要：

  设计并合成了吡啶-苯酚交替低聚物，其中吡啶和苯酚部分通过乙炔键在芳香环的2,6-位交替连接。吡啶氮原子和附近的酚羟基经过定向，因此它们不形成分子内氢键，而是以推挽方式协同作用作为糖的羟基的氢键受体和供体。较长的低聚物与1,2-二氯乙烷中的亲脂性糖苷牢固结合，缔合常数接近10 8  M -1。此外，低聚物从固相到非极性有机溶剂中提取天然糖的程度达到了等量的低聚物的程度，并显示出天然丰富的己糖中甘露糖占主导地位。即使在20％DMSO中的1,2-二氯乙烷中，低聚物也能与天然糖结合，并且对于D-甘露糖和D-葡萄糖显示出大于10 M -1的缔合常数 。

  DOI：

  10.1002/chem.201503149
• 作为产物：
  描述：

  2,6-bis(3-hydroxy-3-methyl-1-butynyl)-4-octoxypyridine 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以62%的产率得到2,6-二乙炔基-4-(辛氧基)吡啶
  参考文献：
  名称：

  Saccharide Recognition-Induced Transformation of Pyridine−Pyridone Alternate Oligomers from Self-Dimer to Helical Complex

  摘要：

  Co-oligomers involving (1H)-4-pyridone and 4-alkoxypyridine rings were studied, and it was found that their supramolecular transformation was caused by saccharide recognition-In the co-oligomers, pyridone and pyridine rings are alternately linked at their 2,6-position with an acetylene bond. The pyridine rings behave as a hydrogen bonding acceptor, and the pyridone rings and tautomerized 4-pyridinol work as a donor. Pyridine-pyridone-pyridine 3-mer was found to self-dimerize on the basis of vapor pressure osmometry in CHCl3, and the association constant was obtained as 2.3 x 10(3) M-1 by H-1 NMR titration. Longer 5-, 7-, 9-, and 11-mer oligomers showed considerable broadening and anisotropy in the H-1 NMR spectra due to self-association. These longer oligomers recognized octyl beta-D-glucopyranoside and changed their form into a chiral helical complex, showing characteristic circular dichroism.

  DOI：

  10.1021/jo800599w

文献信息

• Development of convergent synthetic method for saccharide-linked ethynylpyridine foldamers by Huisgen reaction
  作者：Hajime Abe、Hiroki Makida、Masahiko Inouye

  DOI：10.1016/j.tet.2012.02.069

  日期：2012.6

  Based on 'click chemistry', the new convergent synthesis to a variety of saccharide-linked 2,6-pyridylene ethynylene 'ethynylpyridine' foldamers was developed. Ethynylpyridine 6-, 9-, and 12-meric blocks were linked with 1,7-octadiyne linker block by Sonogashira reaction, and joined with azido group-introduced glucoside, galactoside, and mannoside templates by Huisgen reaction. The resulting saccharide-linked ethynylpyridine foldamers exhibited typical circular dichroism to indicate the formation of a helical structure by intramolecular hydrogen bonds. (C) 2012 Elsevier Ltd. All rights reserved.
• A D3h-Symmetric Macrocycle Alternatingly Composed of Pyridine and Benzyl Alcohol Units Linked with Acetylene Bonds
  作者：Hajime Abe、Ryuta Yumoto、Masahiko Inouye

  DOI：10.3987/com-15-s(t)44

  日期：——

  A macrocyclic compound alternatingly composed of three pyridine and three benzyl alcohol units linked with acetylene bonds was developed as a new type of D-3h-symmetric hexagonal shape-persistent macrocycles with a host function. The macrocycle was prepared via several steps of Sonogashira reaction and proved to interact with halide anions, especially chloride on the basis of H-1 NMR studies.