2-(acetoxymethyl)-9-methyl-1,10-phenanthroline | 118896-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(acetoxymethyl)-9-methyl-1,10-phenanthroline
• 英文别名: 2-Acetoxymethyl-9-methyl-1,10-phenanthroline；(9-methyl-1,10-phenanthrolin-2-yl)methyl acetate
• CAS: 118896-78-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: JZGUHAWVTMFBEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(acetoxymethyl)-9-methyl-1,10-phenanthroline 在 乙醇 、 potassium carbonate 作用下， 反应 6.0h， 生成 (9-甲基-1,10-菲咯啉-2-基)甲醇
  参考文献：
  名称：

  由原位切伦科夫辐射介导的能量转移实现的离散发光镧系配合物的多重和体内光学成像

  摘要：

  最近，我们率先将放射性核素的切伦科夫辐射 (CR) 应用于离散 Eu(III) 和 Tb(III) 配合物的原位激发。CR 是由同位素在介电介质中带电粒子的发射下衰变产生的，并表现出低于 400 nm 的最大强度。我们已经证明，发光的镧系元素天线配合物是切伦科夫辐射介导的能量转移 (CRET) 的理想受体。在这里，我们结合正电子发射放射性同位素18的 CRET 激发开发和评估了肽功能化的 Tb(III) 和 Eu(III) 复合物F 用于同步、多重成像和体内光学成像。这项工作首次表明，在体内检测离散 Eu(III) 复合物的发光是可行的。我们的研究结果为离散的发光镧系元素配合物提供了可能性，这些配合物可用作肿瘤切除术中引导的诊断、光学工具。

  DOI：

  10.1021/jacs.1c04264
• 作为产物：
  描述：

  新铜试剂 在 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(acetoxymethyl)-9-methyl-1,10-phenanthroline
  参考文献：
  名称：

  由原位切伦科夫辐射介导的能量转移实现的离散发光镧系配合物的多重和体内光学成像

  摘要：

  最近，我们率先将放射性核素的切伦科夫辐射 (CR) 应用于离散 Eu(III) 和 Tb(III) 配合物的原位激发。CR 是由同位素在介电介质中带电粒子的发射下衰变产生的，并表现出低于 400 nm 的最大强度。我们已经证明，发光的镧系元素天线配合物是切伦科夫辐射介导的能量转移 (CRET) 的理想受体。在这里，我们结合正电子发射放射性同位素18的 CRET 激发开发和评估了肽功能化的 Tb(III) 和 Eu(III) 复合物F 用于同步、多重成像和体内光学成像。这项工作首次表明，在体内检测离散 Eu(III) 复合物的发光是可行的。我们的研究结果为离散的发光镧系元素配合物提供了可能性，这些配合物可用作肿瘤切除术中引导的诊断、光学工具。

  DOI：

  10.1021/jacs.1c04264

文献信息

• Polypyridine Fluorescent labels for immunoassay
  申请人：Eastman Kodak Company

  公开号：US04837169A1

  公开（公告）日：1989-06-06

  There are described stable fluorescent labels comprising a complex of Eu.sup.+3 and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of Eu.sup.+3 and at least two heteroatom-containing groups which form coordinate complexes with Eu.sup.+3 and a third heteroatom-containing group or heteroatom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, haptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.

  本文描述了稳定的荧光标记物，其中包括Eu.sup.+3和螯合剂的复合物，该螯合剂包括一个三重态敏化剂核，其三重态能量大于Eu.sup.+3，并且至少有两个含杂原子的基团与Eu.sup.+3形成配位络合物，以及第三个杂原子含量的基团或附加到三重态敏化剂中的杂原子。还描述了用于特定结合分析的标记生理活性材料，例如标记的抗原、半抗原、抗体、激素等，其中包括吸附或与稳定荧光标记物结合的生理活性材料。
• Terpyridine chelating agents
  申请人：Eastman Kodak Company

  公开号：US04859777A1

  公开（公告）日：1989-08-22

  There are described stable fluorescent labels comprising a complex of Eu.sup.+3 and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of Eu.sup.+3 and at least two heteroatom-containing groups which form coordinate complexes with Eu.sup.+3 and a third heteroatom-containing group or heteroatom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, haptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.

  描述了稳定的荧光标记物，包括Eu.sup.+3和螯合剂的复合物，其中螯合剂包括一个三重态敏化剂的核，其三重态能量大于Eu.sup.+3，并且至少有两个含杂原子的基团与Eu.sup.+3形成配位络合物，以及第三个含杂原子的基团或杂原子附加到三重态敏化剂上。还描述了标记的生理活性物质，用于特定结合测定，如标记的抗原、半抗原、抗体、激素等，其中包括吸附或结合到稳定荧光标记物上的生理活性物质。
• Fluorescent labels
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0288256A2

  公开（公告）日：1988-10-26

  There are described stable fluorescent labels comprising a complex of Eu⁺³ and a chelating agent comprising a nucleus which is a triplet sensi­tizer having a triplet energy greater than that of Eu⁺³ and at least two heteroatom-containing groups which form coordinate complexes with Eu⁺³ and a third heteroatom-containing group or heteroatom in or appended to the triplet sensitizer which chelating agents are polypyridine or phenanthroline compounds. Labeled physio- logically active materials useful in specific binding assays such as labeled antigens, haptens, antibodies, hormones and the like comprising the stable fluores-cent labels having physiologically active materials adsorbed or bonded thereto are also described.

  所述的稳定荧光标签由 Eu⁺³和螯合剂复合物组成，螯合剂包括一个核，该核是三重能敏化剂，其三重能大于 Eu⁺³的三重能，以及至少两个含杂原子的基团，这些基团与 Eu⁺³形成配位复合物，以及三重能敏化剂中或附加在三重能敏化剂上的第三个含杂原子的基团或杂原子，螯合剂是聚吡啶或菲罗啉化合物。此外，还描述了在特定结合试验中有用的标记生理活性材料，如标记抗原、抗原、抗体、激素等，这些材料包括吸附或结合有生理活性材料的稳定荧光标记。
• Novel Phenanthroline-Containing Trinuclear Double-Stranded Helicates:  Self-Recognition between Helicates with Phenanthroline and Bipyridine Binding Sites
  作者：Mazi Shaul、Yoram Cohen

  DOI：10.1021/jo9908905

  日期：1999.12.1

  The ligands 6,6'-bis[(2-methyl-1,10-phenanthrolin-9-yl)methylenoxymethylenyl] 2,2'-bipyridine (1)- and 2,9-bis[(2-methyl-1,10-phenanthrolin-9-yl)methylenoxymethylenyl]-1,10-phenanthroline (2) were prepared and shown to self-assemble into double-stranded [(L)(2)Cu-3](3+)-type helicates upon reaction with Cu+. Although the reaction of 1 with AgCF3SO3 afforded the double-stranded helicate [(1)(2)Ag-3](3+), reaction of 2 with this salt yielded a mixture of several complexes, all of apparently double-strand nature, based on their diffusion coefficients. Addition of a large excess of AgCF3SO3 afforded [(2)(2)Ag-3](3+) as the sole product. In addition, it was found that the reaction of Cu+ with mixtures of 1 and 6 ",6'''-bis[(6-methyl-2,2'-bipyridin-6'-yl)methylenoxymethylenyl]-2 ",2'''-bipyridine (4) or of 2 with 2,9-bis[(6-methyl-2,2-bipyridin-6'-yl)methylenoxymethylenyl]-1,10-phenanthroline (3) afforded mixtures of homoleptic and heteroleptic helicates. Helicate distribution seems to follow statistical expectations. Mixing of the double-stranded copper helicates of 2 and 3 in DMSO-d(6) afforded, after 2 weeks, a statistical mixture of the homoleptic and heteroleptic helicates, i.e., [(2)(2)Cu-3](3+), [(3)(2)Cu-3](3+), and [(2/3)Cu-3](3+). However, a statistical mixture was obtained within minutes from the double-stranded silver helicates of 2 and 3 in CD3CN. We conclude therefore that even 2 and 3, which contain three phenanthroline and three bipyridine binding sites, are not "sufficiently instructed" to avoid the formation of a heteroleptic helicate in the course of their self-assembly process.
• Chemistry of heterocyclic compounds. 124. Mono-.alpha.-functionalization of 2,9-dimethyl-1,10-phenanthroline
  作者：George R. Newkome、Kevin J. Theriot、Vinod K. Gupta、Frank R. Fronczek、Gregory R. Baker

  DOI：10.1021/jo00268a055

  日期：1989.3