N,N′-bis(2-hydroxyethyl)-2,9-dicarboxamide-1,10-phenanthroline | 1042682-87-0

• 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: N,N′-bis(2-hydroxyethyl)-2,9-dicarboxamide-1,10-phenanthroline
• 英文别名: 2,9-bis(2-hydroxyethylamide)-1,10-phenanthroline；2-N,9-N-bis(2-hydroxyethyl)-1,10-phenanthroline-2,9-dicarboxamide
• CAS: 1042682-87-0
• 化学式: C₁₈H₁₈N₄O₄
• 分子量: 354.365
• InChiKey: CZAKFHSYPNKDKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N′-bis(2-hydroxyethyl)-2,9-dicarboxamide-1,10-phenanthroline 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 以44%的产率得到[1,10]Phenanthroline-2,9-dicarboxylic acid 2-({2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-amide) 9-[(2-hydroxy-ethyl)-amide]
  参考文献：
  名称：

  Hairpin Mimics with Phenanthroline- and Bipyridine-Derived Linkers

  摘要：

  The synthesis and structural stabilities of modified oligonucleotide hairpins containing phenanthroline- and bipyridine-modified loops is reported. Phenanthroline (phen) and bipyridine (bipy) building blocks were synthesized, incorporated into DNA-oligonucleotides, and analyzed by thermal denaturation experiments. The so modified oligomers were found to form stable hairpin structures. Tm values were not affected by divalent transition metals.

  DOI：

  10.1080/15257770701508026
• 作为产物：
  描述：

  1,10-邻二氮杂菲-2,9-二甲酸 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 N,N′-bis(2-hydroxyethyl)-2,9-dicarboxamide-1,10-phenanthroline
  参考文献：
  名称：

  通过水相和有机竞争萃取选择性分离镅 (III)、锔 (III) 和镧系元素 (III)

  摘要：

  将亲水配体添加到水溶液中以选择性结合锕系元素 (III) 被认为是 Ln(III)/An(III) 分离的先进策略。鉴于次锕系元素的回收和放射性废物处理，迫切需要设计和开发合适的配体来选择性分离An(III)和Ln(III)。在此，设计并合成了四种源自吡啶和菲咯啉骨架的具有软硬杂化供体的新型亲水配体，作为水相中 An(III) 选择性络合的掩蔽剂。利用已知的N , N , N ', N '-四辛基二甘醇酰胺(TODGA)作为有机相中的亲脂性萃取剂萃取Ln(III)，提出了竞争萃取An(III)和Ln( III)是基于TODGA和上述亲水配体开发的。最佳亲水配体N , N '-双(2-羟乙基)-2,9-二甲酰胺-1,10-菲咯啉 (2OH-DAPhen) 对 Am(III) 的选择性优于 Ln(III)，浓度为HNO 3的浓度范围为0.05至3.0 M。Eu/Am的最大分离因子高达1365，Eu/Cm的最大分离因子为417

  DOI：

  10.1021/acs.inorgchem.3c03331

文献信息

• Binding of Europium(III) to a Non-Nucleosidic Phenanthroline Linker in DNA
  作者：Ching-Hui Huang、Austin Parish、Florent Samain、Florian Garo、Robert Häner、Janet R. Morrow

  DOI：10.1021/bc900386w

  日期：2010.3.17

  Eu(III) complexes of DNA containing a non-nucleosidic linker, a derivative of 1,10-phenanthroline-2,6- (Q), are studied with the goal of forming novel lanthanide ion binding sites that are incorporated in the backbone of DNA. One oligonucleotide is short and unstructured (TTTQTTT (QT6)) and the other (5'-AGCTCGGTCAQCGAGAGTGCA-3' (SQ)) is studied both in single-stranded form and in the presence of a partially complementary DNA strand. Luminescence spectroscopy studies show, that Eu(III) binds to SQ, QT6, AQB, or QB 1100-, 56-, 23-, or 27-fold more tightly, respectively, that to a simple 1,10-phenanthroline-2,6-dicarboxamide ligand (QI). Direct excitation and phenanthroline sensitized luminescence spectroscopy supports binding of Eu(III) to the phenanthroline linker in QT6 and in double-stranded DNA formed from SQ and partially complementary sequences that place Q in a bulge-like position. Eu(III) hydration numbers range from 3 to 5 when bound to the phenanthroline moiety in modified DNA, consistent with binding to the tetradentate linker and, in some cases, coordination to other in the DNA. Thermal melting experiments show that Q in a bulge-like structure stabilizes double-stranded DNA and that Eu(III) binding does not markedly affect the stability of the duplex.
• Hairpin Mimics with Phenanthroline- and Bipyridine-Derived Linkers
  作者：Gapian Bianké、Robert Häner

  DOI：10.1080/15257770701508026

  日期：2007.11.26

  The synthesis and structural stabilities of modified oligonucleotide hairpins containing phenanthroline- and bipyridine-modified loops is reported. Phenanthroline (phen) and bipyridine (bipy) building blocks were synthesized, incorporated into DNA-oligonucleotides, and analyzed by thermal denaturation experiments. The so modified oligomers were found to form stable hairpin structures. Tm values were not affected by divalent transition metals.
• Selective Separation of Americium(III), Curium(III), and Lanthanide(III) by Aqueous and Organic Competitive Extraction
  作者：Qiang Wu、Huaixin Hao、Yang Liu、Lei-Tao Sha、Wei-Jia Wang、Wei-qun Shi、Zhipeng Wang、Ze-Yi Yan

  DOI：10.1021/acs.inorgchem.3c03331

  日期：2024.1.8

  selective binding of actinides(III) is acknowledged as an advanced strategy in Ln(III)/An(III) separation. In view of the recycling and radioactive waste disposal of the minor actinide, there remains an urgent need to design and develop the appropriate ligand for selective separation of An(III) from Ln(III). Herein, four novel hydrophilic ligands with hard–soft hybrid donors, derived from the pyridine and

  将亲水配体添加到水溶液中以选择性结合锕系元素 (III) 被认为是 Ln(III)/An(III) 分离的先进策略。鉴于次锕系元素的回收和放射性废物处理，迫切需要设计和开发合适的配体来选择性分离An(III)和Ln(III)。在此，设计并合成了四种源自吡啶和菲咯啉骨架的具有软硬杂化供体的新型亲水配体，作为水相中 An(III) 选择性络合的掩蔽剂。利用已知的N , N , N ', N '-四辛基二甘醇酰胺(TODGA)作为有机相中的亲脂性萃取剂萃取Ln(III)，提出了竞争萃取An(III)和Ln( III)是基于TODGA和上述亲水配体开发的。最佳亲水配体N , N '-双(2-羟乙基)-2,9-二甲酰胺-1,10-菲咯啉 (2OH-DAPhen) 对 Am(III) 的选择性优于 Ln(III)，浓度为HNO 3的浓度范围为0.05至3.0 M。Eu/Am的最大分离因子高达1365，Eu/Cm的最大分离因子为417