5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid methyl ester | 459218-48-5

• 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: 5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid methyl ester
• 英文别名: Methyl 2,6-bis(5-methylpyridin-2-yl)pyridine-4-carboxylate；methyl 2,6-bis(5-methylpyridin-2-yl)pyridine-4-carboxylate
• CAS: 459218-48-5
• 化学式: C₁₉H₁₇N₃O₂
• 分子量: 319.363
• InChiKey: KWJZQOHSUBRCAW-UHFFFAOYSA-N

物化性质

• 沸点：
  504.4±50.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以10%的产率得到5,5''-bis(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylic acid methyl ester
  参考文献：
  名称：

  Multi-functionalized 2,2′:6′,2′′-Terpyridines

  摘要：

  在这篇论文中，Stille 型交叉偶联程序被证明是制备各种官能化特吡啶的一种简单而通用的方法。它们可以通过在吡啶外环和中心环的 4′-位上添加不同的取代基一步完成官能化，从而得到多官能化合物。最初得到的甲酯和乙酯基团可以简单地转化为溴甲基和羟甲基基团，从而进行进一步的官能化反应。

  DOI：

  10.1055/s-2002-25357
• 作为产物：
  描述：

  2,6-二氯吡啶-4-羰酰氯 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 50.0h， 生成 5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid methyl ester
  参考文献：
  名称：

  Functionalized 2,2‘-Bipyridines and 2,2‘:6‘,2‘ ‘-Terpyridines via Stille-Type Cross-Coupling Procedures

  摘要：

  Stille-type cross-coupling procedures are utilized in order to prepare a variety of fanctionalized 2,2'-bipyridines and 2,2':6',2"-terpyridines. Such N-heterocyclic compounds are of great interest as chelating ligands for transition-metal ions in the field of supramolecular chemistry. Various mono- and disubstitued 2,2'-bipyridines were synthesized in high yields and multigram scales using a modular design principle. The terpyridines may be functionalized in one step with different substituents at the outer pyridine rings and at the 4'-position of the centered ring, leading to multifunctionalized compounds. The initially obtained methyl ester and ethyl ester groups can be simply converted into bromomethyl and hydroxymethyl groups which allow further functionalization reactions.

  DOI：

  10.1021/jo0260600

文献信息

• Functionalized 2,2‘-Bipyridines and 2,2‘:6‘,2‘ ‘-Terpyridines via Stille-Type Cross-Coupling Procedures
  作者：Marcel Heller、Ulrich S. Schubert

  DOI：10.1021/jo0260600

  日期：2002.11.1

  Stille-type cross-coupling procedures are utilized in order to prepare a variety of fanctionalized 2,2'-bipyridines and 2,2':6',2"-terpyridines. Such N-heterocyclic compounds are of great interest as chelating ligands for transition-metal ions in the field of supramolecular chemistry. Various mono- and disubstitued 2,2'-bipyridines were synthesized in high yields and multigram scales using a modular design principle. The terpyridines may be functionalized in one step with different substituents at the outer pyridine rings and at the 4'-position of the centered ring, leading to multifunctionalized compounds. The initially obtained methyl ester and ethyl ester groups can be simply converted into bromomethyl and hydroxymethyl groups which allow further functionalization reactions.
• Multi-functionalized 2,2′:6′,2′′-Terpyridines
  作者：Marcel Heller、Ulrich S. Schubert

  DOI：10.1055/s-2002-25357

  日期：——

  In this contribution, Stille-type cross-coupling procedure is shown to be an easy and universal way to prepare a variety of functionalized terpyridines. They may be functionalized in one step with different substituents at the outer pyridine rings and at the 4′-position of the centered ring, leading to multi-functionalized compounds. The initially obtained methylester and ethylester groups may be simply converted into bromomethyl and hydroxymethyl groups, which allow further functionalization reactions.

  在这篇论文中，Stille 型交叉偶联程序被证明是制备各种官能化特吡啶的一种简单而通用的方法。它们可以通过在吡啶外环和中心环的 4′-位上添加不同的取代基一步完成官能化，从而得到多官能化合物。最初得到的甲酯和乙酯基团可以简单地转化为溴甲基和羟甲基基团，从而进行进一步的官能化反应。