2,6-二乙炔基-4-(甲氧基甲氧基)吡啶 | 1032413-30-1

• 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-(甲氧基甲氧基)吡啶
• 英文名称: 2,6-diethynyl-4-(methoxymethoxy)pyridine
• 英文别名: 2,6-diethynyl-4-(methoxymethyl)pyridine
• CAS: 1032413-30-1
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: LUBRUGUCGHDWNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二乙炔基-4-(甲氧基甲氧基)吡啶 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.92h， 生成 2,6-bis[2-[6-ethynyl-4-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]pyridin-2-yl]ethynyl]-1H-pyridin-4-one
  参考文献：
  名称：

  Selective Binding of D_2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside

  摘要：

  A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH2Cl2, the host molecule associated with dodecyl beta-maltoside much more strongly K-a = 1.4 x 10(6) M-1) than with octyl monohexosides (K-a = ca. 2 x 10(3) to 1 x 10(4) M-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.

  DOI：

  10.1021/jo2003055
• 作为产物：
  描述：

  2,6-二溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 Oxone 、 potassium fluoride 、 copper(l) iodide 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 水 、 sodium hydride 、 二异丙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 生成 2,6-二乙炔基-4-(甲氧基甲氧基)吡啶
  参考文献：
  名称：

  Rate enhancement of hexose sugar oxidation on an ethynylpyridine-functionalized Pt/Al2O3 catalyst with induced chirality

  摘要：

  在功能化的乙炔吡啶（EPy）-铂/铝氧化物催化剂上，实现了对六碳糖选择性氧化反应的速率提升。EPy配体与六碳糖反应物之间的宿主- guest相互作用生成了一种在催化剂表面引发手性复杂的复合物。

  DOI：

  10.1039/c3cc43482f

文献信息

• Saccharide Recognition-Induced Transformation of Pyridine−Pyridone Alternate Oligomers from Self-Dimer to Helical Complex
  作者：Hajime Abe、Hiroshi Machiguchi、Shinya Matsumoto、Masahiko Inouye

  DOI：10.1021/jo800599w

  日期：2008.6.1

  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.