2-Thiopicolino-(m-methylanilid) | 33262-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Thiopicolino-(m-methylanilid)
• 英文别名: 2-Thiopicolino-m-toluidide；2-Thiopicolino-m-toluodinid；N-(2-Thiopicolinoyl)-m-toluidin；pyridine-2-carbothioic acid 3-methyl-anilide；pyridine-2-carbothioic acid m-toluidide；Pyridin-2-thiocarbonsaeure-m-toluidid；2-Pyridinecarbothioamide, N-(3-methylphenyl)-；N-(3-methylphenyl)pyridine-2-carbothioamide
• CAS: 33262-64-5
• 化学式: C₁₃H₁₂N₂S
• 分子量: 228.318
• InChiKey: UWUXHAPDFSIUMX-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  364.8±44.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Thiopicolino-(m-methylanilid) 在 sodium hydroxide 、 水 、 potassium hexacyanoferrate(III) 作用下， 生成 7-methyl-2-pyridin-2-yl-benzothiazole
  参考文献：
  名称：

  Hisano,T.; Yabuta,Y., Chemical and pharmaceutical bulletin, 1973, vol. 21, p. 511 - 517

  摘要：

  DOI：
• 作为产物：
  描述：

  碳酸甲丙酯 、 3-甲基苯胺 在 sodiumsulfide nonahydrate 、 sulfur 作用下， 反应 72.0h， 生成 2-Thiopicolino-(m-methylanilid)
  参考文献：
  名称：

  带有N，S螯合硫代羧酰胺的阳离子芳烃钌（II）配合物：醇的合成，结构，表征和催化氧化

  摘要：

  一系列构象刚性半夹心反磁性阳离子有机钌（II）配合物与通式的[Ru（η 6 - p -cymene）（ASPH 3）（L）] [其中，L =吡啶-2-硫代甲酰胺配体]有从的[Ru（η的反应合成了6 - p氯-cymene）2 ] 2与二齿配位体硫代甲和ASPH 3 2 M比：在甲醇中在1。所有芳烃钌（II）配合物均已通过FT-IR，1 H NMR和UV-Vis光谱以及元素分析得到了充分表征。的复合物之一的[Ru（η的固态结构6 - p（ASPH -cymene）3）（L4）] BPh 4已经通过单晶X射线晶体学确定。此外，已经研究了在N-甲基吗啉-N-氧化物存在下伯和仲醇氧化成它们相应的醛和酮的情况下，络合物（4）之一的催化效率。

  DOI：

  10.1016/j.jorganchem.2011.10.018

文献信息

• Efficient and recyclable Ru(II) arene thioamide catalysts for transfer hydrogenation of ketones: Influence of substituent on catalytic outcome
  作者：Appukutti Kanchanadevi、Rengan Ramesh、David Semeril

  DOI：10.1016/j.jorganchem.2016.02.016

  日期：2016.4

  The ruthenium(II) complexes have been examined for the transfer hydrogenation of various aromatic, heterocycle and cyclic ketones. The formation of ruthenium(II) hydride is confirmed by 1H- NMR and is proposed as the catalytic intermediate in this reaction. Under the optimized conditions, these ruthenium complexes served as excellent catalyst precursors which smoothly reduce the ketones with conversion

  六个阳离子钌（II）芳烃与分子通式的硫代酰胺络合物的[Ru（η 6 - p -cymene）（PPH 3）（L）] + [其中，L =吡啶-2-硫代酰胺和它的衍生物]已成功从的[Ru（反应合成η 6 - p氯-cymene）2 ] 2与螯合配体的硫代酰胺和PPH 3 2 M比分别为：在1在甲醇中。所有的复合物分离，为他们的BPH 4 -的盐，并通过分析和光谱（FT-IR，UV-Vis和被完全表征11 H-NMR）方法。复合物中的一个的固态结构，的[Ru（η 6 - p -cymene）（PPH 3）（L4）] BPH 4（4）（L4 =  ñ - （2，4，6-三甲基苯基）吡啶已通过X射线单晶衍射建立了2-硫代羧酰胺），表明复合物中存在伪八面体（钢琴凳）配位几何。已经研究了钌（II）配合物对各种芳族，杂环和环状酮的转移氢化作用。氢化钌（II）的形成由1确认1 H-NMR被提出作为该反应中的
• Studies on organosulfur compounds. XI. Selective cyclization to benzothiazole by the reaction between quinaldine and meta-substituted anilines (or nitro compounds) under the modified Willgerodt-Kindler reaction.
  作者：TAKUZO HISANO、MASATAKA ICHIKAWA

  DOI：10.1248/cpb.22.2051

  日期：——

  In order to clarify in more detail the cyclization mechanism of thioanilides to benzothiazoles under the modified Willgerodt-Kindler reaction condition, quinaldine (I) was heated with meta-substituted anilines (II) or meta-substituted nitrobenzenes (III) in the presence of sulfur. Further, in order to examine on solvent effects through these processes, dimethylformamide (DMF) was employed. Although the yields of these reactions were different, the reactions also gave similarly thioanilides and one of the two possible benzothiazoles. The latter was proved to have the structure of 5-substituted 2-(2-quinolyl) benzothiazoles (V) by independent synthesis. On the other hand, the expected two isomeric benzothiazoles (V and VI) were obtained from the oxidaitve cyclization of thioanilides (IV) by the modified Jacobson reaction. Moreover, the thioanilides obtained from I or 2-picoline were found to react with the corresponding II in the presence of sulfur in DMF at 160-170°to give the selective cyclization product, respectively.

  为了更详细地阐明硫代苯胺在改良的 Willgerodt-Kindler 反应条件下生成苯并噻唑的环化机理，在硫存在的情况下，将喹哪啶（I）与元取代苯胺（II）或元取代硝基苯（III）一起加热。此外，为了通过这些过程研究溶剂的影响，还使用了二甲基甲酰胺（DMF）。虽然这些反应的产率不同，但都得到了类似的硫代苯胺和两种可能的苯并噻唑中的一种。通过独立合成，证明后者具有 5-取代的 2-（2-喹啉基）苯并噻唑（V）的结构。另一方面，通过改进的雅各布森反应，硫代苯胺（IV）氧化环化得到了预期的两种异构体苯并噻唑（V 和 VI）。此外，还发现由 I 或 2-甲基吡啶得到的硫代苯胺与相应的 II 在 DMF 中于 160-170° 硫存在下发生反应，分别得到选择性环化产物。
• Bidentate Chelate Compounds. I
  作者：Francis Lions、Kenneth V. Martin

  DOI：10.1021/ja01540a020

  日期：1958.4
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 8.15, page 998 - 1009
  作者：

  DOI：——

  日期：——
• DNA/protein interaction and cytotoxicity of palladium(II) complexes of thiocarboxamide ligands
  作者：Elangovan Sindhuja、Rengan Ramesh、Nallasamy Dharmaraj、Yu Liu

  DOI：10.1016/j.ica.2014.03.002

  日期：2014.5

  Four planar palladium(II) complexes with general formula [Pd(Cl)(L)(PPh3)] (HL = N-substituted pyridine-2- thiocarboxamide) have been synthesized and characterized by analytical, spectral (IR, UV-Vis and H-1, C-13 and P-31 NMR) and single crystal X-ray methods. Crystal structure of all the complexes indicated a mono negative bidentate coordination of thiocarboxamide ligands to the palladium center via pyridine nitrogen and thiol sulfur and reveals a square planar geometry. The interaction of palladium(II) thiocarboxamide complexes with calf thymus DNA (CT-DNA) studied by absorption and emission spectroscopic methods revealed that complexes 5-8 could interact with CT-DNA through intercalation. Further, the interaction of the palladium complexes with bovine serum albumin (BSA) was investigated using UV-Vis, fluorescence and synchronous fluorescence methods. The tryptophan and tyrosine residues in BSA as model protein was quenched by the complexes in a static quenching process. The radical scavenging ability of all the complexes was accessed by in vitro antioxidant assays involving DPPH radical, hydroxyl radical, nitric oxide radical and ABTS radicals and was found to be excellent. Further, the anti-cancer activity of complexes 5-8 against HeLa, MCF-7 and NIH-3T3 cell line has been studied. Though the complexes 5, 6 and 8 showed more potent anticancer activity than cisplatin, complex 5 was found to be superior. (C) 2014 Elsevier B.V. All rights reserved.