2,6-bis(((2-mercaptophenyl)amino)methyl)pyridine | 173106-02-0

• 分子结构分类: 有机化合物
• 英文名称: 2,6-bis(((2-mercaptophenyl)amino)methyl)pyridine
• 英文别名: 2,6-bis(2-mercaptophenylamino)dimethylpyridine；2,6-bis(2-mercaptophenylaminomethyl)pyridine；pyN2H2S2-H2；2-[[6-[(2-Sulfanylanilino)methyl]pyridin-2-yl]methylamino]benzenethiol
• CAS: 173106-02-0
• 化学式: C₁₉H₁₉N₃S₂
• 分子量: 353.512
• InChiKey: YXAOFFJTIGMIHX-UHFFFAOYSA-N

物化性质

• 沸点：
  537.8±50.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  zinc perchlorate 、 2,6-bis(((2-mercaptophenyl)amino)methyl)pyridine 在 NaOH 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Brand, Udo; Burth, Rainer; Vahrenkamp, Heinrich, Inorganic Chemistry, 1996, vol. 35, # 4, p. 1083 - 1086

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[6-(2,3-Dihydro-1,3-benzothiazol-2-yl)pyridin-2-yl]-2,3-dihydro-1,3-benzothiazole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以88%的产率得到2,6-bis(((2-mercaptophenyl)amino)methyl)pyridine
  参考文献：
  名称：

  源自杂环和2-巯基乙胺的五齿混合二硫醇盐螯合配体的合成

  摘要：

  2，6-吡啶二醛与2-巯基乙胺或2-烷基硫代乙胺的缩合产生2，6-双（取代的2-噻唑烷基）吡啶或2，6-双-（（（2-烷基-硫代）乙基亚氨基）甲基吡啶。噻唑烷可以还原地打开，得到2，6-双-（（取代的-2-硫代乙基）氨基甲基）吡啶。或者，后者可以通过2，6-吡啶二醛与2-巯基乙胺的还原胺化来合成。2，5-噻吩二羰基氯与2-巯基乙胺的反应生成N，N′-双（取代的-2-硫乙基）-2，5-噻吩二甲酰胺。2,6-双-（（取代-2-硫乙基）氨基甲基）吡啶和N，N'-双（取代-2-硫乙基）-2,5-噻吩二甲酰胺是新颖的五齿混合物 可以形成具有仿生重要性的铁配合物的二硫醇盐螯合剂。

  DOI：

  10.1016/s0040-4039(99)00757-1

文献信息

• Substitution and redox reactions of mono- and dinuclear ruthenium complexes containing the ligand
  作者：D. Sellmann、S.Y. Shaban、A. Rösler、F.W. Heinemann

  DOI：10.1016/j.ica.2004.12.004

  日期：2005.3

  In quest of ruthenium complexes having [RuN 3 S 2 ] cores, a non-flexible configuration, trans -thiolate donors and exchangeable coligand L, [Ru(L)(pyN 2 H 2 S 2 )] complexes have been synthesized [ pyN 2 H 2 S 2 2 - = 2 , 6 - bis ( 2 - mercaptophenylaminomethyl ) pyridine ( 2 - ) ] . Treatment of [RuCl 2 (CH 3 CN) 4 ] with pyN 2 H 2 S 2 2 - gave [Ru(py)(pyN 2 H 2 S 2 )] ( 1 ). The pyridine coligand

  为了寻求具有[RuN 3 S 2]核的钌配合物，已经合成了非柔性构型，反式硫醇盐供体和可交换大肠菌L，[Ru（L）（pyN 2 H 2 S 2）]配合物[pyN 2 H 2 S 2 2-= 2，6-双（2-巯基苯基氨基甲基）吡啶（2-）]。用pyN 2 H 2 S 2 2处理[RuCl 2（CH 3 CN）4]-得到[Ru（py）（pyN 2 H 2 S 2）]（1）。吡啶大分子1在实践中证明是不稳定的，可以在正常条件下被CO或DMSO取代，得到[Ru（CO）（pyN 2 H 2 S 2）]（2）和[Ru（DMSO）（pyN 2 H 2 S 2）]（3）。或者，可以在[CO]存在下直接从[RuCl 2（CH 3 CN）4]和pyN 2 H 2 S 2 2-中获得2，而在没有CO的情况下反应得到双核[Ru（pyN 2 H 2 S 2）] 2（8）。用NOBF 4处理2或3得到[Ru III（CO）（pyN
• Transition Metal Complexes with Sulfur Ligands. 136.¹ Enforced Trans Coordination of Thiolate Donors in Electron Rich Iron, Ruthenium, and Nickel [M(L)(pyN₂H₂S₂)] and [M(L)(pyS₄)] Complexes (L = CO, PPh₃, DMSO) (pyN₂H₂S₂^2- = 2,6-Bis(2-mercaptophenylamino)dimethylpyridine(2−); pyS₄^2- = 2,6-Bis(2-mercaptophenylthio)dimethylpyridine(2−))
  作者：Dieter Sellmann、Jürgen Utz、Frank W. Heinemann

  DOI：10.1021/ic990169h

  日期：1999.11.1

  In the course of a systematic study of transition metal complexes exhibiting three properties, electron rich metal centers, con structures with trans thiolate donors, and the capability to bind nitrogenase related small molecules, the pentadentate ligands pyN(2)H(2)S(2)-H-2 (=2,6-bis(2-mercaptophenylamino)dimethylpyridine) and pyS(4)-H-2 (=2,6-bis(2-mercaptophenylthio)dimethylpyridine) have been synthesized. Alkylation of 2(3H)-benzothiazolone by 2,6-bis[(tosyloxy)methyl]pyridine and subsequent alkaline hydrolysis yielded pyN(2)H(2)S(2)-H-2 (3). Template alkylation of [Ni(S2C6H4)(2)](2-) (6) by 2,6-bis[(tosyloxy)methyl] pyridine gave [Ni(pyS(4))](2) (7) whose acidic hydrolysis yielded pyS(4)-H-2. HCl (9). The reaction of Fe(II) salts with pyN(2)H(2)S(2)(2-) gave [Fe(pyN(2)H(2)S(2))] (10). Five-coordinate 10 is paramagnetic (mu(eff) (293 K) 5.34 mu(B)), has a trigonal bipyramidal structure, and coordinates CO to give diamagnetic [Fe(CO)(pyN(2)H(2)S(2))] fill. Although the nu(CO) of 11 (1928 cm(-1) (KBr)) indicates electron rich Fe centers and strong Fe-CO bonds, 11 readily dissociated CO in solution. Reactions of pyN(2)H(2)S(2)(2-) with ruthenium precursor complexes yielded diamagnetic [Ru(L)(pyN(2)H(2)S(2))], (L DMSO (12), PPh3 (13), or CO (14)) which have practically substitution inert Ru-L bonds. Only 12 could be converted into 14 under drastic conditions (140 bar CO, 120 degrees C, 12 h, THF). Methylation of the thiolate donors to give [Ru(L)(pyN(2)H(2)S(2)-Me-2)]I-2 (L = DMSO (15) and PPh3 (16)) did not labilize the Ru-L bonds. The reaction of Fe(II) salts with pyS(4)(2-) in the presence of CO yielded [Fe(CO)(pyS(4))] (17). Complex 17 has a higher nu(CO) (1955 cm(-1) in KBr) than 11 but is stable toward Fe-CO dissociation. The spectroscopic data of all synthesized complexes and X-ray structure analyses of 7, 10, 13, 15, 16, and 17 showed that all six-coordinate [M(L)(pyN(2)H(2)S(2))] and [M(L)(pyS(4))] complexes uniformly have C-2 symmetrical core structures and trans thiolate donors, thus differing from analogous complexes of pentadentate NxHxSy2- ligands (x + y = 5) whose [MNxSy] cores exhibit either C-S or C-1 symmetry and cis or trans thiolate donors. The nu(CO) frequencies in homologous [Fe(CO)(NxHxSy)] complexes (x + y = 5) showed that exchange of aromatic thioether S for amine NH donors considerably increases the electron density at the iron centers. A minor influence was observed for the exchange of aliphatic thioether S for NH donors or changes of the [FeNxSy] core structures.
• Chen, Xiaoyuan; Femia, Frank J.; Babich, John W., Inorganica Chimica Acta, 2000, vol. 310, p. 237 - 241
  作者：Chen, Xiaoyuan、Femia, Frank J.、Babich, John W.、Zubieta, Jon

  DOI：——

  日期：——