6,6''-diacetyl-2,2':6',2''-terpyridine | 874942-55-9

• 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
• 英文名称: 6,6''-diacetyl-2,2':6',2''-terpyridine
• 英文别名: 6,6''-bis-acetyl-2,2':6'2''-terpyridine；1-[6-[6-(6-acetylpyridin-2-yl)pyridin-2-yl]pyridin-2-yl]ethanone
• CAS: 874942-55-9
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: MBKLMHAAYJDLKB-UHFFFAOYSA-N

物化性质

• 熔点：
  192-194 °C(Solv: ethanol (64-17-5))
• 沸点：
  522.3±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.81
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6,6''-diacetyl-2,2':6',2''-terpyridine 、 2,6-二异丙基苯胺 在 甲酸 作用下， 反应 0.58h， 以60%的产率得到6,6''-bis(iminoacetyl)-2,2':6',2''-terpyridine-bis(2,6-diisopropylanil)
  参考文献：
  名称：

  Use of Stille-type cross-coupling as a route to oligopyridylimines

  摘要：

  The new tin reagents, 2-(n-Bu3Sn)-6-(C(R)OCH2CH2O)-C5H3N, (R=H a, Me b), have been employed in Stille-type cross-coupling reactions with a range of oligopyridylbromides generating, following a facile deprotection step, a series of formyl- and acetyl-functionalised oligopyridines. Condensation reactions with 2,6-diisopropylaniline has allowed access to families of novel sterically bulky multidentate N,N,N,N (tetradentate), N,N,N,N,N (pentadentate), N,N,N,N,N,N (sexidentate) and N,N,N,N,N,N,N (heptadentate) nitrogen donor ligands. This work represents a straightforward and rapid synthetic route for the preparation of oligopyridylimines, which are expected to act as useful components for the self-assembly of polymetallic complexes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.137
• 作为产物：
  描述：

  6,6''-Bis-(2-methyl-[1,3]dioxolan-2-yl)-[2,2';6',2'']terpyridine 在 盐酸 作用下， 生成 6,6''-diacetyl-2,2':6',2''-terpyridine
  参考文献：
  名称：

  Use of Stille-type cross-coupling as a route to oligopyridylimines

  摘要：

  The new tin reagents, 2-(n-Bu3Sn)-6-(C(R)OCH2CH2O)-C5H3N, (R=H a, Me b), have been employed in Stille-type cross-coupling reactions with a range of oligopyridylbromides generating, following a facile deprotection step, a series of formyl- and acetyl-functionalised oligopyridines. Condensation reactions with 2,6-diisopropylaniline has allowed access to families of novel sterically bulky multidentate N,N,N,N (tetradentate), N,N,N,N,N (pentadentate), N,N,N,N,N,N (sexidentate) and N,N,N,N,N,N,N (heptadentate) nitrogen donor ligands. This work represents a straightforward and rapid synthetic route for the preparation of oligopyridylimines, which are expected to act as useful components for the self-assembly of polymetallic complexes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.137

文献信息

• Mono- vs. bi-metallic assembly on a bulky bis(imino)terpyridine framework: a combined experimental and theoretical study
  作者：Yohan D. M. Champouret、Jean-Didier Maréchal、Ishaq Dadhiwala、John Fawcett、Donna Palmer、Kuldip Singh、Gregory A. Solan

  DOI：10.1039/b516083a

  日期：——

  ligands, 6,6''-(2,6-i-Pr2C6H3)N=CR}2-2,2':6',2''-C15H9N3 (R = H L1, Me L2), have been prepared in high yield from the condensation reaction of the corresponding carbonyl compound with two equivalents of 2,6-diisopropylaniline. The molecular structure of L2 reveals a transoid relationship between the imino and pyridyl nitrogen groups throughout the ligand framework. Treatment of aldimine-containing L1 with

  双（亚氨基）三联吡啶配体，6,6''-（2,6-i-Pr2C6H3）N = CR} 2-2,2'：6'，2''-C15H9N3（R = H L1，Me通过相应的羰基化合物与两个当量的2，6-二异丙基苯胺的缩合反应，可以高收率制备L2）。L2的分子结构揭示了整个配体框架中亚氨基和吡啶基氮基团之间的反式关系。在110摄氏度下，在n-BuOH中用一当量或过量的MX2处理含醛亚胺的L1，得到单核五配位络合物[（L1）MX2]（M = Fe，X = Cl 1a; M = Ni， X ＝ Br 1b； M ＝ Zn，X ＝ Cl 1c），其中金属中心占据了联吡啶的腔并且亚氨基基团是侧基。相反，含酮亚胺的L2与过量的MX2在正丁醇中于110摄氏度反应，得到双核络合物，[（L2）M2X4]（M = Fe，X = Cl 3a； M = Ni，X = Br 3b； M = Zn，X = Cl 3c），其中一