5LIO-1,2-HOPO | 910106-58-0

• 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: 5LIO-1,2-HOPO
• 英文别名: 1-hydroxy-N-[2-[2-[(1-hydroxy-6-oxopyridine-2-carbonyl)amino]ethoxy]ethyl]-6-oxopyridine-2-carboxamide
• CAS: 910106-58-0
• 化学式: C₁₆H₁₈N₄O₇
• 分子量: 378.342
• InChiKey: CPYNOZVPXTXSTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5LIO-1,2-HOPO 、 europium(III) chloride hexahydrate 在 吡啶 作用下， 以 甲醇 为溶剂， 以89%的产率得到[Eu(5LIO-1,2-HOPO)2](1-)
  参考文献：
  名称：

  “Cymothoe sangaris”:  An Extremely Stable and Highly Luminescent 1,2-Hydroxypyridinonate Chelate of Eu(III)

  摘要：

  The synthesis, structure, and characterization of a new class of luminescent agents based on the 1,2-hydroxypyridinone chelator are reported. The prototype complex, [Eu(5LIO-1,2-HOPO)2]-, demonstrates superb aqueous stability [pEu = 18.64(10)] and is highly emissive [Phit = 0.21(3)], emitting almost pure "red" light (lambdaem = 612 nm). The crystal structure reveals a coordination geometry reminiscent of a "butterfly", hence the soubriquet of "Cymothoe sangaris" to identify with the unique species of red butterfly found only in Central Africa.

  DOI：

  10.1021/ja062597+
• 作为产物：
  描述：

  6-氧代-1-苯基甲氧基吡啶-2-羧酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 5LIO-1,2-HOPO
  参考文献：
  名称：

  “Cymothoe sangaris”:  An Extremely Stable and Highly Luminescent 1,2-Hydroxypyridinonate Chelate of Eu(III)

  摘要：

  The synthesis, structure, and characterization of a new class of luminescent agents based on the 1,2-hydroxypyridinone chelator are reported. The prototype complex, [Eu(5LIO-1,2-HOPO)2]-, demonstrates superb aqueous stability [pEu = 18.64(10)] and is highly emissive [Phit = 0.21(3)], emitting almost pure "red" light (lambdaem = 612 nm). The crystal structure reveals a coordination geometry reminiscent of a "butterfly", hence the soubriquet of "Cymothoe sangaris" to identify with the unique species of red butterfly found only in Central Africa.

  DOI：

  10.1021/ja062597+

文献信息

• LUMINESCENT 1-HYDROXY-2-PYRIDINONE CHELATES OF LANTHANIDES
  申请人：Raymond Kenneth N.

  公开号：US20100015725A1

  公开（公告）日：2010-01-21

  The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.

  本发明提供了一种含有1,2-羟基吡啶酮基团的有机配体和镧系离子之间的发光配合物。该发明的配合物在水溶液中稳定，并且可用作分子探针，例如在医学诊断和生物分析测量系统中。本发明还提供了使用所述配合物的方法。
• Correlation of Structural and Magnetic Properties in a Set of Mononuclear Lanthanide Complexes
  作者：Peter Comba、Lena J. Daumann、Rüdiger Klingeler、Changhyun Koo、Mark J. Riley、Asha E. Roberts、Hubert Wadepohl、Johannes Werner

  DOI：10.1002/chem.201704822

  日期：2018.4.6

  The electronic and magnetic properties of a set of mononuclear terbium(III) and dysprosium(III) complexes with two tetradentate 1‐hydroxy‐pyridin‐2‐one (1,2‐HOPO) ligands are reported. Two primary coordination geometries are observed, depending on the length of the linker between the 1,2‐HOPO donor moieties and the resulting arrangements of the linker. Fine details of the magnetic circular dichroism

  报道了一组具有两个四齿1-羟基-吡啶-2-1-2（1,2-HOPO）配体的单核ter（III）和（III）配合物的电子和磁性。根据1,2-HOPO供体基团之间的接头长度和接头的最终排列，观察到两个主要的配位几何。III（III）配合物的磁性圆二色性（MCD）光谱的精细细节说明了J分裂的差异多重，并允许进行彻底的配体场分析。（（III）配合物的高频电子顺磁共振（HF-EPR）研究可洞悉基态的组成。从头算是用来合理化实验结果，并进一步说明结构特征对不同配合物的电子和磁性的影响。
• Highly Luminescent Lanthanide Complexes of 1-Hydroxy-2-pyridinones
  作者：Evan G. Moore、Jide Xu、Christoph J. Jocher、Ingrid Castro-Rodriguez、Kenneth N. Raymond

  DOI：10.1021/ic702144n

  日期：2008.4.1

  photophysical properties of several trivalent lanthanide complexes formed from two differing bis-bidentate ligands incorporating either alkyl or alkyl ether linkages and featuring the 1-hydroxy-2-pyridinone (1,2-HOPO) chelate group in complex with Eu(III), Sm(III), and Gd(III) are reported. The Eu(III) complexes are among some of the best examples, pairing highly efficient emission (Phi tot (Eu) approximately

  几种三价镧系元素配合物的合成、X 射线结构、稳定性和光物理性质，这些配合物由两种不同的双二齿配体形成，结合烷基或烷基醚键并具有 1-羟基-2-吡啶酮 (1,2-HOPO)螯合基团与 Eu(III)、Sm(III) 和 Gd(III) 形成复合物。Eu(III) 复合物是一些最好的例子之一，在水溶液中将高效发射（Phi tot (Eu) 约 21.5%）与高稳定性（pEu 约 18.6）配对，是用于生物测定的绝佳候选者。观察到的具有不同主链连接的复合物行为的比较显示出显着的相似性，无论是稳定性还是光物理特性。Gd(III) 复合物的低温光物理测量也用于深入了解电子结构，并发现与模型复合物的相应时间相关密度泛函理论 (TD-DFT) 计算一致。由于观察到的固态结构的动态旋转，溶液中和单晶中高分辨率 Eu(III) 发射光谱的比较也揭示了溶液中金属离子更对称的配位几何。
• Luminescent 1-Hydroxy-2-Pyridinone Chelates of Lanthanides
  申请人：The Regents of The University of California

  公开号：EP2511266A1

  公开（公告）日：2012-10-17

  The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.

  本发明提供了镧系元素离子与含有 1,2-羟基吡啶酮单元的有机配体之间的发光复合物。本发明的配合物在水溶液中稳定，可用作分子探针，例如用于医疗诊断和生物分析检测系统。本发明还提供了使用本发明复合物的方法。
• US8557601B2
  申请人：——

  公开号：US8557601B2

  公开（公告）日：2013-10-15