4-n-butoxy-2,6-dibromopyridine | 173314-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-n-butoxy-2,6-dibromopyridine
• 英文别名: 2,6-dibromo-4-butoxypyridine
• CAS: 173314-96-0
• 化学式: C₉H₁₁Br₂NO
• 分子量: 309.0
• InChiKey: UXQWSZDBMIHBFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.5±37.0 °C(Predicted)
• 密度：
  1.638±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-n-butoxy-2,6-dibromopyridine 在 copper(l) iodide bis-triphenylphosphine-palladium(II) chloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 sodium hydride 、 二乙胺 、 二异丙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  非手性合成氢键低聚物中手性螺旋的糖依赖诱导

  摘要：

  众所周知，生物聚合物的构象转变受与小分子的非共价相互作用的影响。我们发现合成聚合物，聚和低聚（间乙炔基吡啶），通过不带电荷的氢键与聚合物内球体中封闭的糖类相互作用而被引导到螺旋结构。圆二色性 (CD) 研究表明，糖的手性转移到聚合物的螺旋意义上。在天然重要的己糖的正辛基吡喃糖苷中，β-葡萄糖苷最有效地诱导 CD。尺寸调节的 18 聚体和更长的低聚物也显示出与聚合物相似的诱导 CD。此外，在聚合物的帮助下，天然单糖被提取到极性较小的有机溶剂中，诱导类似的 CD 信号。

  DOI：

  10.1021/ja039371g
• 作为产物：
  描述：

  4-丁氧基-2,6-吡啶二甲酸 在 1-氧化-2-巯基吡啶 、 4-二甲氨基吡啶 、 三氯溴甲烷 、 N,N'-二环己基碳二亚胺 作用下， 反应 6.0h， 以33%的产率得到4-n-butoxy-2,6-dibromopyridine
  参考文献：
  名称：

  Molecular Recognition of .beta.-Ribofuranosides by Synthetic Polypyridine-Macrocyclic Receptors

  摘要：

  Artificial ribofuranoside receptors were designed and synthesized. The design of the polypyridine-macrocyclic receptors was based on the multipoint hydrogen bond complementarity between the receptors and methyl beta-D-ribofuranoside. The binding affinity of the receptors for the ribofuranoside in CDCl3 was very high (up to K-a = 5.2 x 10(3) M(-1)), so that even native ribose was extracted by them into such nonpolar solvents. Selective extraction of ribose by the receptors\was observed: the extractabilities, or affinities to the receptors of various pentoses and hexoses decreased in the following order: ribose > deoxyribose congruent to lxyose congruent to xylose > fructose > arabinose > glucose congruent to mannose congruent to galactose. The selectivity is governed by the OH direction and the whole size of the sugars as well as their shapes. Furthermore, fluorescence emission of the receptors was largely enhanced in the presence of methyl beta-D-ribofuranoside or ribose, and the degree for the fluorescence enhancement by the addition of various sugars was almost compatible with that of the extractabilities. The polypyridine-macrocycles represent rationally designed multifunctional artificial receptors for ribofuranosides.

  DOI：

  10.1021/ja00155a006

文献信息

• Glucopyranoside Recognition by Polypyridine-Macrocyclic Receptors Possessing a Wide Cavity with a Flexible Linkage
  作者：Masahiko Inouye、Junya Chiba、Hiroyuki Nakazumi

  DOI：10.1021/jo9911138

  日期：1999.10.1

  New polypyridine-macrocyclic receptors for glucopyranosides were designed and synthesized. The artificial receptors possess a terpyridine skeleton asa hydrogen-bonding site and a flexible polyoxyethylene chain as a bridge for the macrocyclic structure, in which the cavity of the receptors is large enough to incorporate pyranosides, The receptors showed high affinities for n-octyl beta-(D)-glucopyranoside, and selective binding of the receptors was observed between epimeric pyranosides. The results obtained in this paper demonstrated versatility of the terpyridine skeleton as a hydrogen-bonding site for saccharides.