2,9-diethynyl-1,10-phenanthroline | 133810-41-0

• 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: 2,9-diethynyl-1,10-phenanthroline
• CAS: 133810-41-0
• 化学式: C₁₆H₈N₂
• 分子量: 228.253
• InChiKey: FSKOOQNFJYCGLA-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±40.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,9-diethynyl-1,10-phenanthroline 在 L-ascorbic acid sodium salt 、 copper(II) sulfate 、 三乙胺 、 N,N-二异丙基乙胺 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 26.5h， 生成 1,1'-((4,4'-(1,10-phenanthroline-2,9-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(propane-3,1-diyl))bis(2',3-diisopropylguanidine) trifluoroacetic acid
  参考文献：
  名称：

  Phenanthroline-2,9-bistriazoles as selective G-quadruplex ligands

  摘要：

  G-quadruplex (G4) ligands are currently receiving considerable attention as potential anticancer therapeutics. A series of phenanthroline-2,9-bistriazoles carrying tethered positive end groups has been synthesized and evaluated as G4 stabilizers. The compounds were efficiently assembled by copper(I)catalyzed azide-alkyne cycloaddition (CuAAC) in CH2Cl2 and water in the presence of a complexing agent. Characterization of the target compounds on telomeric and c-KIT G4 sequences led to the identification of guanidinium-substituted compounds as potent G4 DNA ligands with high selectivity over duplex DNA. The diisopropylguanidium ligands exhibited high selectivity for the proto-oncogenic sequence c-KIT over the human telomeric sequence in the surface plasmon resonance (SPR) assay, whereas the compounds appeared potent on both G4 structures in the FRET melting temperature assay. The phenanthroline-2,9-bistriazole ligands were thus identified as potent G4 ligands with high selectivity over duplex DNA, and preliminary results indicate that the scaffold may form basis for the development of subtype-specific G4 ligands. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.027
• 作为产物：
  描述：

  新铜试剂 在 selenium(IV) oxide 、 水 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 生成 2,9-diethynyl-1,10-phenanthroline
  参考文献：
  名称：

  Novel hydrophilic bistriazolyl-phenanthroline ligands with improved solubility and performance in An/Ln separations

  摘要：

  新开发的 BTrzPhen 配体在水介质中的溶解度更高，对小锕系元素的选择性也有所提高。

  DOI：

  10.1039/d3ra02707d

文献信息

• Towards molecular electronics: a new family of aromatic polyimine chelates substituted with alkyne groups
  作者：Jean Suffert、Raymond Ziessel

  DOI：10.1016/s0040-4039(00)74877-5

  日期：1991.2

  Bromo and chloro polyimines react with trimethylsilyacetylene in the presence of Pd(PPh3)2Cl2/CuI and diisopropylamine to give new substituted polyimines 1a to 8a. These compounds are deprotected with K2CO3 in MeOH / THF to produce the corresponding terminal alkynes 1b to 8b.

  在Pd（PPh 3）2 Cl 2 / CuI和二异丙胺的存在下，溴和氯代聚亚胺与三甲基甲炔反应，得到新的取代的聚亚胺1a至8a。这些化合物在MeOH / THF中用K 2 CO 3脱保护，生成相应的末端炔烃1b至8b。
• General Method for the Preparation of Alkyne-Functionalized Oligopyridine Building Blocks
  作者：Raymond Ziessel、Jean Suffert、Marie-Thérèse Youinou

  DOI：10.1021/jo960538g

  日期：1996.1.1

  diynes provides access to ditopic bipyridine or terpyridine ligands oligoPy(C&tbd1;C)(4)oligoPy comprising a tetrayne spacer. Quantitative formation of air-stable copper(I) complexes is described for the 6,6'-substituted ligands. A single crystal X-ray structure of complex 22a shows that the two ligands are interlocked around the copper(I) center in a pseudotetrahedral arrangement, similar to the structure

  通过用含水甲醇碱处理从其形成末端二炔低聚（C＆tbd1; C）（2）H。oligoPy（C＆tbd1; C）（2）H与BrC＆tbd1; CSiEt（3）的反应产生了甲硅烷基化的三炔oligoPy（C＆tbd1; C）（3）SiEt（3）。进一步的同源性受到炔丙基链C-2碳上正丙胺的亲核攻击的限制，产生顺式/顺式（48％），顺式/反式（33％）和反式/反式（19 ％）烯胺二炔化合物21a-c。末端二炔的Glaser氧化自偶联提供了对包含四炔间隔基的二位联吡啶或三联吡啶配体oligoPy（C＆tbd1; C）（4）oligoPy的访问。描述了6,6'-取代的配体的空气稳定铜（I）配合物的定量形成。配合物22a的单晶X射线结构表明，两个配体以伪四面体排列互锁在铜（I）中心周围，类似于从NMR和FAB（+）数据推导的结构。本文报道的合成方法代表了大规模制备炔基官能化的低聚吡啶的有价值的方法。
• Hydrophilic 2,9-bis-triazolyl-1,10-phenanthroline ligands enable selective Am(<scp>iii</scp>) separation: a step further towards sustainable nuclear energy
  作者：Alyn C. Edwards、Pavle Mocilac、Andreas Geist、Laurence M. Harwood、Clint A. Sharrad、Neil A. Burton、Roger C. Whitehead、Melissa A. Denecke

  DOI：10.1039/c7cc01855j

  日期：——

  consisting of only C, H, O and N atoms for the selective extraction of Am(III) from spent nuclear fuel are reported herein. One of these 2,9-bis-triazolyl-1,10-phenanthroline (BTrzPhen) ligands combined with a non-selective extracting agent, was found to exhibit process-suitable selectivity for Am(III) over Eu(III) and Cm(III), providing a clear step forward.

  本文报道了仅由C，H，O和N原子组成的第一亲水性1,10-菲咯啉衍生的配体，用于从乏核燃料中选择性提取AM（III）。一这些2,9-双-三唑基- 1,10-菲咯啉（BTrzPhen）配体与非选择性萃取剂相结合，被认为表现出过程适合选择性AM（III）在铕（III）和CM（III），这是前进的明确步伐。
• Heteroleptic Copper(I) Complexes Prepared from Mono‐ and Tetra‐phenylbenzene‐substituted Phenanthroline Ligands
  作者：Brigino Ralahy、Uwe Hahn、Emeric Wasielewski、Jean‐François Nierengarten

  DOI：10.1002/ejic.202100331

  日期：2021.7.15

  (L2) substituents have been synthetized and used to prepare bis-phenanthroline copper(I) complexes. Steric constraints are limited in the case of the biphenyl-substituted ligand and [Cu(L1)2](BF4) has been obtained by reaction of L1 with [Cu(CH3CN)4](BF4). In contrast, the tetraarylbenzene substituents of L2 are large enough to totally prevent the formation of the corresponding homoleptic bis-phenanthroline

  带有两个联苯 ( L1 ) 或两个四芳基苯 ( L2 ) 取代基的菲咯啉配体已被合成并用于制备双菲咯啉铜 (I) 配合物。在联苯取代的配体的情况下，空间约束受到限制，并且 [Cu( L1 ) 2 ](BF 4 ) 已通过L1与 [Cu(CH 3 CN) 4 ](BF 4 ) 的反应获得。相比之下，L2的四芳基苯取代基大到足以完全阻止相应的均配双菲咯啉铜 (I) 配合物的形成。两者L1和L2还与 2,9-二甲基-1,10-菲咯啉 (dmp) 结合制备相应的杂配双菲咯啉铜 (I) 配合物。从L1和L2获得的所有铜 (I) 配合物都显示了几种阻转异构体之间的动态构象交换。已经进行了详细的核磁共振研究和密度泛函理论 (DFT) 计算，以评估它们在溶液中的构象。
• CN117186069
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  公开号：——

  公开（公告）日：——