4-丁氧基-2,6-吡啶二甲酸 | 173314-95-9

• 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
• 中文名称: 4-丁氧基-2,6-吡啶二甲酸
• 中文别名: 4-丁氧基-2,6-吡啶二羧酸
• 英文名称: 4-butoxypyridine-2,6-dicarboxylic acid
• CAS: 173314-95-9
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: KUUDOGYXZGMCRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  96.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二丁基4-丁氧基吡啶-2,6-二羧酸酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以70%的产率得到4-丁氧基-2,6-吡啶二甲酸
  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

• Intramolecular hydrogen bonding studies for a series of dipurinyl-2,6-pyridinedicarboxamides
  作者：Geoffrey T. Crisp、Yu-Lin Jiang

  DOI：10.1016/s0040-4020(98)01053-9

  日期：1999.1

  A series of potential receptor molecules based on the dipurinyl-2,6-pyridinedicarboxamide motif has been prepared and the intramolecular hydrogen bonding characterised by 1H NMR and FT-IR spectroscopies. The hydrogen bonding gives rise to a preferential planar, cis conformation for the molecules. The planar nature of the unit also gives rise to π-π stacking as shown by 1H NMR dilution experiments.

  制备了一系列基于二嘌呤基-2,6-吡啶二甲酰胺基序的潜在受体分子，并通过1 H NMR和FT-IR光谱对分子内氢键进行了表征。氢键对分子产生优先的平面顺式构象。单元的平面性质也引起π-π堆积，如1 H NMR稀释实验所示。
• Highly selective adenine recognition by a macrocyclic host molecule employing multiple hydrogen bonding and π–π stacking interactions
  作者：Yosuke Hisamatsu、Haruka Takami、Naohiro Shirai、Shin-ichi Ikeda、Kazunori Odashima

  DOI：10.1016/j.tetlet.2006.11.106

  日期：2007.1

  A new macrocyclic host, which contains a 2,6-bis(oxazol-2-yl)pyridine unit and a 2,7-dialkoxynaphthalene unit tethered by the appropriate length of alkyl side chains is prepared. This host undergoes highly selective complex formation with an adenine nucleobase, accompanied by a fluorescence response in CHCl3 by a combination of multiple hydrogen bonding and π–π stacking interactions.

  制备了一种新的大环主体，该主体包含一个2,6-双（恶唑-2-基）吡啶单元和一个2,7-二烷氧基萘单元，并通过适当的烷基侧链长度进行束缚。该宿主与腺嘌呤核碱基经历高度选择性的复合物形成，伴随有多个氢键和π-π堆积相互作用的结合，在CHCl 3中产生荧光响应。
• Conformational restriction by intramolecular hydrogen bonding. Carbohydrate-carbohydrate self-assembly
  作者：Manuela López de la Paz、Gary Ellis、Soledad Penadés、Cristina Vicent

  DOI：10.1016/s0040-4039(97)00156-1

  日期：1997.3

  NMR data (chemical shifts, NOEs, coupling constants and variable temperature experiments), FT-IR data and MM2(.) molecular mechanics calculations have allowed us to demonstrate that 3-amido-1,6-anhydro-3-deoxy-beta-D-glucopyranose acts as a hydroxyl-based interaction unit and provides conformational control of self-recognition processes by intramolecular hydrogen bonding. (C) 1997 Elsevier Science Ltd.