吡嗪并[2,3-f][4,7]菲咯啉 | 217-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 吡嗪并[2,3-f][4,7]菲咯啉
• 英文名称: 4',7'-phenanthrolino-5,6:5',6'-pyrazine
• 英文别名: Pyrazino[2,3-f][4,7]phenanthroline
• CAS: 217-82-3
• 化学式: C₁₄H₈N₄
• 分子量: 232.244
• InChiKey: NVFJXZGVAGNQDD-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C
• 沸点：
  486.0±40.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 吡嗪并[2,3-f][4,7]菲咯啉 以 甲醇 为溶剂， 以81%的产率得到fac-(ppz)(Re(CO)3Cl)2
  参考文献：
  名称：

  Yoblinski; Stathis, Michael; Guarr, Thomas F., Inorganic Chemistry, 1992, vol. 31, # 1, p. 5 - 10

  摘要：

  DOI：
• 作为产物：
  描述：

  泛喹酮 在 palladium on activated charcoal 盐酸羟胺 、 一水合肼 、 barium carbonate 作用下， 以 乙醇 为溶剂， 反应 23.5h， 生成 吡嗪并[2,3-f][4,7]菲咯啉
  参考文献：
  名称：

  Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives

  摘要：

  Condensation of 5,6-diamino-4,7-phenanthroline with glyoxal provides 1,4,5,12-tetraazatriphenylene in quantitative yield. This procedure avoids the 50% loss of product inherent in previous methods. Derivatives were also prepared by using alpha-dicarbonyl compounds other than glyoxal. Additional derivatives were prepared from 1,4,5,12-tetraazatriphenylene-2,3-dicarbonitrile, produced by condensation of diaminomaleonitrile with 4,7-phenanthroline-5,6-dione.

  DOI：

  10.1021/jo0495283

文献信息

• Intervalence charge transfer in a “chain-like” ruthenium trinuclear assembly based on the bridging ligand 4,7-phenanthrolino-5,6:5′,6′-pyrazine (ppz)
  作者：Deanna M. D'Alessandro、F. Richard Keene

  DOI：10.1039/b512625h

  日期：——

  d mixed valence species while the two mixed valence states of the trinuclear complex exhibit localised behaviour. One-electron oxidation of a terminal Ru centre in the trinuclear case gives rise to a broad, low intensity IVCT band for the +7 mixed valence species which is composed of two underlying Gaussian-shaped bands. The transitions are identified as adjacent and remote IVCT transitions, with the

  三核复合物[Delta-Ru（bpy）2} 2 Delta（t）-Ru（bpy）（mu-ppz）2}] n +的混合价形式的IVCT特性[n = 7，8; t =反式），并且双核复合物[Ru（bpy）2} 2（mu-ppz）] 5+的非对映异构体（内消旋和外消旋）对组装的核性和氧化程度显示出显着的依赖性。双核物种被分类为边界局部-离域混合价种，而三核复合物的两个混合价态表现出局部行为。在三核情况下，末端Ru中心的单电子氧化产生了+7个混合价态物种的宽低强度IVCT带，该带由两个基本的高斯形谱带组成。过渡被识别为相邻和远程IVCT过渡，前者主导了IVCT流形的强度。
• Syntheses, crystal structures and magnetic properties of dinuclear copper(II) complexes with pyrazino[2,3-f  ][4,7]phenanthroline (pap) as bridging ligand
  作者：Hilde Grove、Jorunn Sletten、Miguel Julve、Francesc Lloret

  DOI：10.1039/a907658a

  日期：——

  Three dinuclear copper(II) complexes with pyrazino[2,3-f][4,7]phenanthroline (pap) as bridging ligand have been prepared; [Cu2(pap)(C2O4)2]·5H2O 1, [Cu2(pap)(H2O)7(SO4)]SO4·3H2O 2 and [Cu2(pap)(H2O)3(NO3)3]NO33. These are the first metal complexes of pap which have been characterized by X-ray crystallography and magnetic susceptibility measurements. In 1 the dinuclear complex is intercepted by a mirror plane; the bridging pap and the terminal oxalate ligands are bidentate in the equatorial plane of copper. In addition copper has weak axial interactions to oxygen atoms of oxalate in two neighbouring molecules. In 2 the two crystallograpically independent copper atoms are both six-co-ordinated with bridging pap and water molecules in equatorial positions, the axial positions being occupied by two water molecules or one water molecule and one sulfate oxygen atom, respectively. In 3 the co-ordination geometry of one copper is close to square pyramidal with pap, one nitrate oxygen atom and one water in equatorial positions; another water occupies the apical position. The description of the co-ordination sphere of the other copper is complicated by the presence of disorder in one of the co-ordinated nitrate groups. When considering only the major site of the disordered nitrate, the co-ordination geometry may in a first approximation be described as square pyramidal with a significant trigonal bipyramidal distortion. In the square pyramidal description the two pap nitrogen atoms, one water and one nitrate oxygen constitute the equatorial plane and a nitrate oxygen is situated in apical position. All the co-ordinated nitrate ions have a second weak Cu⋯O interaction. The Cu⋯Cu separations across bridging pap are 6.740 (1), 6.834 (2) and 6.808 Å (3). Variable-temperature susceptibility measurements reveal Curie law behaviour with very weak intramolecular antiferromagnetic coupling in all three compounds, the relevant parameters being J = −1.4 cm−1, g = 2.06 for 1, J = −1.5 cm−1, g = 2.10 for 2, and J = −1.3 cm−1, g = 2.08 for 3 (the Hamiltonian being H = −J SA·SB).

  准备了三种二核铜(II)配合物，使用呫唑并[2,3-f][4,7]菲啰啉（pap）作为桥联配体；分别为[Cu2(pap)(C2O4)2]·5H2O 1、[Cu2(pap)(H2O)7(SO4)]SO4·3H2O 2 和 [Cu2(pap)(H2O)3(NO3)3]NO3。这些是首次通过X射线晶体学和磁化率测量表征的pap金属配合物。在1中，二核配合物被一个镜面平面截断；桥联的pap和末端的草酸配体在铜的赤道平面内是双齿配体。此外，铜还与两个相邻分子的草酸的氧原子存在弱的轴向相互作用。在2中，两种晶体独立的铜原子都被六个配位，桥联的pap和水分子处于赤道位置，轴向位置分别被两个水分子或一个水分子及一个硫酸根氧原子占据。在3中，一个铜的配位几何形状接近于正方体金字塔，配体为pap、一个硝酸根氧原子和一个水分子位于赤道位置；另一个水分子位于顶点位置。另一个铜的配位球的描述因一个配位的硝酸根配体的无序出现而变得复杂。当仅考虑无序硝酸根的主要位点时，配位几何形状可以在初步近似下描述为正方体金字塔，并存在显著的三角双金字塔畸变。在正方体金字塔的描述中，两个pap氮原子、一个水分子和一个硝酸根氧原子构成赤道平面，一个硝酸根氧原子位于顶点位置。所有配位的硝酸根离子都有第二个弱的Cu⋯O相互作用。通过桥联pap的Cu⋯Cu间隔分别为6.740 Å (1)、6.834 Å (2) 和6.808 Å (3)。可变温的磁化率测量揭示出符合居里定律的行为，在三种化合物中，分子内的抗铁磁耦合非常弱，相关参数为1中J = −1.4 cm−1，g = 2.06；2中J = −1.5 cm−1，g = 2.10；3中J = −1.3 cm−1，g = 2.08（哈密顿量为H = −J SA·SB）。
• Spectroscopic and electrochemical properties of dimeric Ruthenium(II) diimine complexes and determination of their excited state redox properties
  作者：Yael Fuchs、Sonita Lofters、Thomas Dieter、Wei Shi、Robert Morgan、Thomas C. Strekas、Harry D. Gafney、A. David Baker

  DOI：10.1021/ja00243a023

  日期：1987.4

  The complexes Ru(bpy)/sub 2/(ppz)/sup 2 +/ and ((bpy)/sub 2/Ru(ppz)Ru(bpy)/sub 2/)/sup 4 +/, where ppz is the planar ligand 4',7'-phenanthrolino-5',6':5,6-pyrazine, have been prepared and characterized. Resonance Raman spectra establish that the visible spectra of Ru(bpy)/sub 2/L/sup 2 +/ and ((bpy)/sub 2/Ru-L-Ru(bpy)/sub 2/)/sup 4 +/ complexes, where L is a bis-diimine, in general, are composed of

  络合物 Ru(bpy)/sub 2/(ppz)/sup 2 +/ 和 ((bpy)/sub 2/Ru(ppz)Ru(bpy)/sub 2/)/sup 4 +/，其中 ppz 是平面配体 4',7'-phenanthrolino-5',6':5,6-pyrazine 已被制备和表征。共振拉曼光谱确定 Ru(bpy)/sub 2/L/sup 2 +/ 和 ((bpy)/sub 2/Ru-L-Ru(bpy)/sub 2/)/sup 4 +/ 的可见光谱复合物，其中 L 是双二亚胺，通常由 MLCT 跃迁组成，这些跃迁终止于位于不同配体上的 ..pi..* 轨道。在室温下在单金属和双金属配合物的流体溶液中可检测到的发光可以指定为 L(..pi..*) ..-->.. Ru(II) t/sub 2 / 过渡。较低能量 MLCT 吸收最大值和发射最大值之间的近似但一般的相关性表明，在许多其他 Ru(II)
• Heilmittelchemische Studien in der heterocyclischen Reihe. 17. Mitteilung. 4,7-Phenanthrolinchinon-Derivate mit amoebicider Wirkung
  作者：P. Schmidt、J. Druey

  DOI：10.1002/hlca.19570400212

  日期：——

  The amebicidal activity of the phenanthroline quinones published earlier2) and of their derivates described in this paper is discussed. The highest activity was found with 4,7-phenanthrolino-5, 6- quinone 1 and its monosemicarbazone 3, which are also active in man. Further derivatives of 1 are described.

  本文讨论了2）之前发表的菲咯啉醌及其衍生物的杀螨活性。发现在人类中也具有活性的4,7-菲咯啉-5、6-醌1及其单半碳环酮3的活性最高。描述了1的其他导数。
• Burning Rate Performance Study of Ammonium Perchlorate Catalyzed by Heteroleptic Copper(I) Complexes with Pyrazino[2,3‐ <i>f</i> ][1,10]phenanthroline‐Based Ligands
  作者：Manuel A. Escobar、Cesar Morales‐Verdejo、Juan Luis Arroyo、Paulina Dreyse、Iván González、Iván Brito、Desmond MacLeod‐Carey、David Moreno da Costa、Alan R. Cabrera

  DOI：10.1002/ejic.202001092

  日期：2021.5.7

  heteroleptic Cu(I) complexes with pyrazino[2,3‐ f ][1,10]phenanthroline‐based ligands ( C1‐7 ) on the thermal decomposition of ammonium perchlorate (AP). The complexes C2 and C4‐7 were synthesized and characterized by NMR, HRMS and, in the case of C7 , by X‐ray diffraction. The burning rate performance of C1‐7 on thermal decomposition of AP was studied by differential scanning calorimetry technique. The effect

  该贡献描述了杂配性Cu（I）与吡嗪并[2,3-f] [1,10]菲咯啉基配体（C1-7）的配合物对高氯酸铵（AP）热分解的催化作用。合成了配合物C2和C4-7，并通过NMR，HRMS进行了表征，对于C7，则通过X射线衍射对其进行了表征。通过差示扫描量热技术研究了C1-7对AP热分解的燃烧速率性能。评估了抗衡离子类型，金属中心数和配体取代的影响。与纯AP相比，这些AP +复杂混合物可降低点火温度，并增加热分解过程中释放的热量。在配合物系列中，化合物C4表现出更高的催化作用，而C5则表现出最高的能量释放，