9,10-phenanthrenequinonethiosemicarbazone | 59851-25-1

• 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-phenanthrenequinonethiosemicarbazone
• 英文别名: 9,10-phenanthraquinone thiosemicarbazone；phenanthraquinone monothiosemicarbazone；phenanthrenequinone thiosemicarbazone；phenanthraquinone thiosemicarbazone；PQTSC；phenanthrene-9,10-dione monothiosemicarbazone；[(10-oxophenanthren-9-ylidene)amino]thiourea
• CAS: 59851-25-1
• 化学式: C₁₅H₁₁N₃OS
• mdl: MFCD14711004
• 分子量: 281.338
• InChiKey: BMKLICMDLLQCGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.48
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9,10-phenanthrenequinonethiosemicarbazone 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [Pd(phenanthrenequinone thiosemicarbazone(1-))Cl]*DMF
  参考文献：
  名称：

  Antitumor Metallothiosemicarbazonates:  Structure and Antitumor Activity of Palladium Complex of Phenanthrenequinone Thiosemicarbazone

  摘要：

  The crystal structure of the potential antitumor metal compound, viz. chloro, mono(phenanthrenequinone thiosemicarbazonato) palladium(II) dimethyl formamide solvate, is reported. The central palladium(II) atom is in a square planar environment provided by the tridentate, monoanionic thiosemicarbazone ligand and the ancillary chloride ion. The compound exhibited remarkable activity against drug-sensitive and drug-resistant breast cancer cell lines and was relatively nontoxic toward the normal mammary epithelial cells. The drug-induced killing effect against breast cancer cell lines was predominantly mediated via apoptosis, a physiologic form of cell death.

  DOI：

  10.1021/ic048214v
• 作为产物：
  描述：

  菲醌 生成 9,10-phenanthrenequinonethiosemicarbazone
  参考文献：
  名称：

  De, Journal of the Indian Chemical Society, 1930, vol. 7, p. 361,364

  摘要：

  DOI：

文献信息

• 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
• 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。
• A Phenanthraquinone Based Fluorescent Probe for Sequential Detection of Cu2+ and SO3 2−
  作者：Saswati Gharami、Deblina Sarkar、Samik Acharyya、Tapan Kumar Mondal

  DOI：10.1007/s10895-016-1907-z

  日期：2016.11

  Herein we report the selective detection of Cu2+ and SO3 2− by phenanthraquinone thiosemicarbazone (PQTSC) chemosensor. The chemosensor is efficient in detecting Cu2+ over other metal ions, while the PQTSC-Cu2+ complex selectively sense SO3 2− over other anions. On addition of Cu2+ to the receptor solution, quenching of emission intensity is observed by 16 folds and upon gradual addition of SO3 2−

  本文中，我们报告了菲咯醌硫代半碳carb（PQTSC）化学传感器对Cu 2+和SO 3 2-的选择性检测。的化学传感器是检测有效的Cu 2+比其他金属离子，而PQTSC铜2+复合物选择性地感SO 3 2-优于其它阴离子。在受体溶液中添加Cu 2+时，观察到发射强度猝灭了16倍，并且在该溶液中逐渐添加SO 3 2-时，发射强度增加并且最大值恢复。通过荧光滴定计算出的Cu 2+检测的检测下限为1.06×10 -8 M和PQTSC与Cu 2+的缔合常数为2.18×10 5。