9,10-phenanthrenequinone-N''-phenylthiosemicarbazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9,10-phenanthrenequinone-N''-phenylthiosemicarbazone
• 英文别名: 1-[(10-oxophenanthren-9-ylidene)amino]-3-phenylthiourea
• 化学式: C₂₁H₁₅N₃OS
• 分子量: 357.436
• InChiKey: XOSAABBWHTXEBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  bis(triphenylphosphine)nickel(II) chloride 、 9,10-phenanthrenequinone-N''-phenylthiosemicarbazone 以 乙醇 为溶剂， 反应 4.0h， 以80%的产率得到[Ni(9,10-phenanthrenequinone-N''-phenylthiosemicarbazone)₂]
  参考文献：
  名称：

  含ONS供体配体的镍（II）配合物：合成，表征，晶体结构和CC交叉偶联反应的催化应用

  摘要：

  镍（II）含有缩氨基硫脲配位体[镍（L）配合物2 ]（1 - 3）（L = 9,10- phenanthrenequinonethiosemicarbazone（HL 1），9,10-菲醌-N-甲硫基缩氨基脲（HL 2）和图9，已通过元素分析和光谱法（IR，UV-Vis，1 H，13 C-NMR和ESI质量）合成并表征了10-菲醌-N-苯基硫代半脲（HL 3）。配合物1和2的分子结构通过单晶X射线衍射分析来鉴定。分析表明，该配合物具有扭曲的八面体几何形状，配体以单负三齿ONS方式进行配位。已经研究了复合物对某些C-C偶联反应（即Kumada-Corriu，Suzuki-Miyaura和Sonogashira）的催化活性。该络合物在Kumada-Corriu和Sonogashira偶联反应中，而不是在Suzuki-Miyaura偶联中，起着高效催化剂的作用。 合成并表征了带有9,10-菲醌N

  DOI：

  10.1007/s12039-015-0811-4
• 作为产物：
  描述：

  苯基氨基硫脲盐酸盐 、 菲醌 以 乙醇 为溶剂， 反应 2.0h， 以87%的产率得到9,10-phenanthrenequinone-N''-phenylthiosemicarbazone
  参考文献：
  名称：

  Synthesis, characterization, DNA interaction, antioxidant and anticancer activity of new ruthenium(II) complexes of thiosemicarbazone/semicarbazone bearing 9,10-phenanthrenequinone

  摘要：

  A new series of octahedral ruthenium(II) complexes supported by tridentate ligands derived from phenanthrenequinone and derivatives of thiosemicarbazide/semicarbazide and other co-ligands have been synthesized and characterized. DNA binding experiments indicated that ruthenium(II) complexes can interact with DNA through non-intercalation and the apparent binding constant value (K-b) of [RuCl(CO)(PPh3)(L-3)] (3) at room temperature was calculated to be 2.27 x 10(3) M-1. The DNA cleavage studies showed that the complexes have better cleavage of pBR 322 DNA. Antioxidative activity proved that the complexes have significant radical scavenging activity against free radicals. Cytotoxic activities showed that the ruthenium(II) complexes exhibited more effective cytotoxic activity against selected cancer cells. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2013.09.005

文献信息

• Palladium(II) 9,10-phenanthrenequinone N-substituted thiosemicarbazone/semicarbazone complexes as efficient catalysts for N-arylation of imidazole
  作者：Panneerselvam Anitha、Rajendran Manikandan、Periasamy Viswanathamurthi

  DOI：10.1080/00958972.2015.1071484

  日期：2015.10.2

  catalytic efficiency of the synthesized complexes was examined against N-arylation of imidazole. The system works well with the electron-rich, -neutral, and -deficient aryl halides to afford the products in good to excellent yields. Sterically congested aryl halides and heteroaryl halides have also been used as substrates to provide N-arylated heterocycles. In addition, this methodology can be applicable

  一系列钯配合物，[PdCl(L1–4)] (1–4) (L1 = 9,10-菲醌缩氨基硫脲，L2 = 9,10-菲醌甲基缩氨基硫脲，L3 = 9,10-菲醌苯硫缩氨基硫脲，和 L3 9,10-菲醌缩氨基脲），已通过元素分析、UV-vis、FT-IR、1H 和 13C NMR 以及 ESI-质谱法进行合成和表征。针对咪唑的N-芳基化检查了合成配合物的催化效率。该系统适用于富含电子的、中性的和缺乏的芳基卤化物，以提供良好到极好的产率的产品。空间拥挤的芳基卤化物和杂芳基卤化物也已用作底物以提供 N-芳基化杂环。此外，该方法可适用于其他具有含氮杂环的底物。
• Ruthenium(II) 9,10-phenanthrenequinone thiosemicarbazone complexes: synthesis, characterization, and catalytic activity towards the reduction as well as condensation of nitriles
  作者：Panneerselvam Anitha、Periasamy Viswanathamurthi、Devarayan Kesavan、Ray Jay Butcher

  DOI：10.1080/00958972.2014.977269

  日期：2015.1.17

  with O, N, and S as the donor sites and are in the thiol form in all the complexes. Catalytic studies showed that all the complexes displayed good catalytic activity towards the reduction of nitriles and also the condensation of nitriles with 2-aminoalcohol under solvent-free conditions. Graphical Abstract

  配体 9,10-菲醌-N4-取代的缩氨基硫脲 (HL1-3) 及其钌 (II) 配合物被合成并通过元素和光谱方法表征。配体是三齿一元螯合配体，以 O、N 和 S 作为供体位点，并且在所有配合物中都是硫醇形式。催化研究表明，所有配合物对腈的还原以及腈与 2-氨基醇在无溶剂条件下的缩合均表现出良好的催化活性。图形概要
• Rhodium(I) complexes containing 9,10-phenanthrenequinone-N-substituted thiosemicarbazone ligands: Synthesis, structure, DFT study and catalytic diastereoselective nitroaldol reaction studies
  作者：P. Anitha、R. Manikandan、P. Vijayan、S. Anbuselvi、P. Viswanathamurthi

  DOI：10.1016/j.jorganchem.2015.06.004

  日期：2015.8

  New rhodium(I) complexes [Rh(CO)(L)] (1–3) were prepared by the reaction of [RhCl(CO)(PPh3)2] with 9,10-phenanthrenequinone-N-substituted thiosemicarbazones (HL1-3) and characterized by elemental and spectral analyses (IR, UV–Vis, 1H and 13C NMR, ESI-Mass). The structure of the complex, [Rh(CO)(L1)] (1) has been established by single-crystal X-ray diffraction analysis. The structure has also been optimized

  新铑（I）配合物的[Rh（CO）（L）]（1 - 3）通过[的RhCl（CO）（PPH反应制备3）2 ]与9,10-菲醌-N-取代缩氨基硫脲（HL 1-3），并通过元素和光谱分析（IR，UV-Vis，1 H和13 C NMR，ESI-Mass）进行表征。配合物的结构[Rh（CO）（L 1）]（1）是通过单晶X射线衍射分析确定的。还使用LANL2DZ基集通过DFT方法对结构进行了优化。在室温下，在离子液体存在下，合成的络合物用作苯甲醛与硝基乙烷的非对映选择性硝基羟醛反应的催化剂。发现优化的催化剂2在各种芳族醛和硝基烷之间的不对称亨利反应中是有效的。在多达五次催化运行中检查了催化剂的可重复使用性。结果表明收率略有损失，产物保留了非对映选择性。相信该方法为容易地合成大量非对映异构富集的β-硝基醇提供了机会。
• Nickel(II) complexes containing ONS donor ligands: Synthesis, characterization, crystal structure and catalytic application towards C-C cross-coupling reactions
  作者：PANNEERSELVAM ANITHA、RAJENDRAN MANIKANDAN、PARANTHAMAN VIJAYAN、GOVINDAN PRAKASH、PERIASAMY VISWANATHAMURTHI、RAY JAY BUTCHER

  DOI：10.1007/s12039-015-0811-4

  日期：2015.4

  Sonogashira coupling reactions rather than Suzuki-Miyaura coupling. Nickel(II) complexes bearing 9,10-phenanthrenequinone N-substituted thiosemicarbazone ligands were synthesized and characterized. The X-ray crystal structure of the complexes revealed a distorted octahedral geometry around the metal centre. These nickel complexes exhibited better catalytic activity in Kumada-Corriu and Sonogashira

  镍（II）含有缩氨基硫脲配位体[镍（L）配合物2 ]（1 - 3）（L = 9,10- phenanthrenequinonethiosemicarbazone（HL 1），9,10-菲醌-N-甲硫基缩氨基脲（HL 2）和图9，已通过元素分析和光谱法（IR，UV-Vis，1 H，13 C-NMR和ESI质量）合成并表征了10-菲醌-N-苯基硫代半脲（HL 3）。配合物1和2的分子结构通过单晶X射线衍射分析来鉴定。分析表明，该配合物具有扭曲的八面体几何形状，配体以单负三齿ONS方式进行配位。已经研究了复合物对某些C-C偶联反应（即Kumada-Corriu，Suzuki-Miyaura和Sonogashira）的催化活性。该络合物在Kumada-Corriu和Sonogashira偶联反应中，而不是在Suzuki-Miyaura偶联中，起着高效催化剂的作用。 合成并表征了带有9,10-菲醌N
• Synthesis, characterization, DNA interaction, antioxidant and anticancer activity of new ruthenium(II) complexes of thiosemicarbazone/semicarbazone bearing 9,10-phenanthrenequinone
  作者：Panneerselvam Anitha、Nataraj Chitrapriya、Yoon Jung Jang、Periasamy Viswanathamurthi

  DOI：10.1016/j.jphotobiol.2013.09.005

  日期：2013.12

  A new series of octahedral ruthenium(II) complexes supported by tridentate ligands derived from phenanthrenequinone and derivatives of thiosemicarbazide/semicarbazide and other co-ligands have been synthesized and characterized. DNA binding experiments indicated that ruthenium(II) complexes can interact with DNA through non-intercalation and the apparent binding constant value (K-b) of [RuCl(CO)(PPh3)(L-3)] (3) at room temperature was calculated to be 2.27 x 10(3) M-1. The DNA cleavage studies showed that the complexes have better cleavage of pBR 322 DNA. Antioxidative activity proved that the complexes have significant radical scavenging activity against free radicals. Cytotoxic activities showed that the ruthenium(II) complexes exhibited more effective cytotoxic activity against selected cancer cells. (C) 2013 Elsevier B.V. All rights reserved.