1,4-bis(o-aminophenylthio)butane | 58044-70-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-bis(o-aminophenylthio)butane
• 英文别名: 1,4-bis(o-aminothiophenol)butane；1,4-bis (o-aminophenyl)disulfide butane；1,4-Bis-(2-aminophenylthio)-butan；1,4-di(o-aminobenzenethio)butane；[2-({4-[(2-aminophenyl)thio]butyl}thio)phenyl]amine；2,2'-[1,4-butanediylbis(thio)]bisbenzenamine；1,4-bis(2-aminophenylthio)butane；2-[4-(2-aminophenyl)sulfanylbutylsulfanyl]aniline
• CAS: 58044-70-5
• 化学式: C₁₆H₂₀N₂S₂
• 分子量: 304.48
• InChiKey: LZFSCAODXJRLAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  477.9±30.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(o-aminophenylthio)butane 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 2,2'-[1,4-butanediylbis(thio)]bisbenzenamine dihydrochloride
  参考文献：
  名称：

  QSAR modeling, synthesis and bioassay of diverse leukemia RPMI-8226 cell line active agents

  摘要：

  A rigorous QSAR modeling procedure employing CODESSA PRO descriptors has been utilized for the prediction of more efficient anti-leukemia agents. Experimental data concerning the effect on leukemia RPMI-8226 cell line tumor growth of 34 compounds (treated at a dose of 10 mu M) was related to their chemical structures by a 4-descriptor QSAR model. Four bis(oxy)bis-urea and bis(sulfanediyl)bis-urea derivatives (4a, 4b, 8, 11a) predicted as active by this model, together with 11b predicted to be of low activity, were synthesized and screened for anti-tumor activity utilizing 55 different tumor cell lines. Compounds 8 and 11a showed anti-tumor properties against most of the adopted cell lines with growth inhibition exceeding 50%. The highly promising preliminary anti-tumor properties of compounds 8 and 11a, were screened at serial dilutions (10(-4)-10(-8) mu M) for determination of their GI(50) and TGI against the screened human tumor cell lines. Compound 11a (GI(50) = 1.55, TGI = 8.68 mu M) is more effective than compound 8 (GI(50) = 58.30, TGI = >100 mu M) against the target leukemia RPMI-8226 cell line. Compound 11a also exhibits highly pronounced anti-tumor properties against NCI-H226, NCI-H23 (non-small cell lung cancer), COLO 205 (colon cancer), SNB-75 (CNS cancer), OVCAR-3, SK-OV-3 (ovarian cancer), A498 (renal cancer) MDA-MB-231/ATCC and MDA-MB-468 (breast cancer) cell lines (GI(50) = 1.95, 1.61, 1.38, 1.56, 1.30, 1.98, 1.18, 1.85, 1.08, TGI = 8.35, 6.01, 2.67, 8.59, 4.01, 7.01, 5.62, 6.38, 5.63 mu M, respectively). Thus 11a could be a suitable lead towards the design of broad spectrum anti-tumor active agents targeting various human tumor cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.033
• 作为产物：
  描述：

  1,4-二溴丁烷 、 2-氨基苯硫醇 在 zinc(II) oxide 作用下， 以 neat (no solvent) 为溶剂， 以88%的产率得到1,4-bis(o-aminophenylthio)butane
  参考文献：
  名称：

  用于 CS 键构建的氧化锌催化无溶剂机械化学路线：可持续的过程

  摘要：

  已经开发了氧化锌催化的无溶剂机械化学路线，通过亲核取代（SN2 机制）使用各种硫醇和苯甲酰/苄基/烷基溴化物快速构建 CS 键。这种方法的显着优点包括广泛的底物范围、更清洁的反应曲线、安全、可扩展、环境条件下的高产率和催化剂的重复使用。此外，制备的合成前体是各种生物活性分子合成中的重要组成部分。

  DOI：

  10.1002/ejoc.201601425

文献信息

• Bis(2-cyanoacetamides): versatile precursors for bis(dihydropyridine-3,5-dicarbonitriles)
  作者：Sherif M. H. Sanad、Ahmed H. M. Elwahy、Ismail A. Abdelhamid

  DOI：10.24820/ark.5550190.p010.683

  日期：——

  5-dicarbonitriles) containing thioether linkages are prepared via the condensation of bis(cyanoacetamides) with α-substituted cinnamonitriles in the presence of piperidine. The target compounds can also be obtained via a three-component reaction of bis(cyanoacetamides) with two equivalents of both aldehydes and malononitrile in ethanol containing piperidine as a base.

  含有硫醚键的双（6-氨基-1,2-二氢吡啶-3,5-二甲腈）是通过双（氰基乙酰胺）与α-取代的肉桂腈在哌啶存在下的缩合反应制备的。目标化合物也可以通过双（氰基乙酰胺）与两当量的醛和丙二腈在含有哌啶作为碱的乙醇中的三组分反应获得。
• Synthesis and DFT Calculations of Dinuclear Complex of Co2+, Ni2+ and Cu2+ with Macrocyclic Schiff base Ligands
  作者：Eid Al-Razaq、Nabeel Buttrus、Enas Mohammed、Abdel Jbarah

  DOI：10.13005/ojc/320114

  日期：2016.3.28

  The 20-, 34and 36-membered macrocyclic of bis (dithiodimine) Schiff base ligands, BisN,N’(dithiocarbonyl) terephthliden (L1), Bis-N,N’[1,3(o-aminophenylthio)-propane] terephthylidene (L2) and Bis-N,N-[1,4(o-amino phenylthio)-butane] terephthylidene (L3), have been prepared by a (2+2) condensation of terephthaldehyde with dithiooxamide or 1,3-bis-(o-aminophnylthio) propane,or1,4-bis-(o-aminophenylethio)-butane

  双（二硫代二胺）席夫碱配体，BisN，N'（二硫代羰基）对苯二甲酸（L1），Bis-N，N'[1,3（邻氨基苯硫基）-丙烷]对苯二甲基（20、34和36元大环L2）和Bis-N，N- [1,4（邻氨基苯硫基）丁烷]对苯二亚甲基（L3）是通过对苯乙醛与二硫代草酰胺或1,3-双-（（邻氨基苯硫基丙烷）或1,4-双-（邻氨基苯硫基）丁烷。金属盐与L1，L2和L3在四氢呋喃中的反应获得了Co2 +，Ni2 +和Cu2 +的空气稳定双核配合物。配体由两个与金属离子配位的S2N2供体位点组成。另外，还提出了钴配合物与1，4-苯二甲胺的加合物。CHN元素分析，金属含量，摩尔电导率，磁测量，质子核磁共振，紫外可见光谱和红外光谱研究已经表征了络合物和加合物。除此之外，DFT即密度泛函理论计算已用于支持实验数据。该过程使用了B3LYP功能方法。这是由Yang，Parr和Lee引入的方法。由于存在Axel Be
• Ring-size and substituent effects in relatively rigid macrocyclic quinquedentate ligands. Structure determinations of [ZnL⁴(H₂O)₂][ClO₄]₂·MeCN and [ZnL³(ClO₄)₂]
  作者：David C. Liles、Mary McPartlin、Peter A. Tasker

  DOI：10.1039/dt9870001631

  日期：——

  spectroscopic evidence show that the 15- and 16-membered ring ligands form seven-co-ordinate complexes in which the macrocycle defines the equatorial plane of an approximate pentagonal bipyramid and the axial sites are occupied by water molecules or co-ordinated anions. The geometry of the N3X2-donor set (X = O or S) and hence the goodness of fit for different metal ions depends crucially on the nature

  从吡啶-2,6-二甲醛与α，ω-二苯胺之间的环缩合反应中分离出二十一个具有N 5-，N 3 O 2-和N 3 S 2-供体的大环五齿配体金属配合物[例如1 ，2-二（邻氨基苯硫基）乙烷]是在二价过渡金属盐的存在下进行的。X [ZNL的仪射线结构分析3（CLO 4）2 ]和[ZNL 4（H 2 O] [CLO 4 ] 2 ·的MeCN（L 3 =二氢-6,7- 15,19-nitrilodibenzo [e，p ] [1,4,7,15]-二硫杂氮杂环庚素，L 4 = 7,8-二氢-6 H -16,20-硝酰二苯并[ f，q ]-[1,5,8,16]二硫杂氮杂环-十八烷基）和光谱证据表明，15和16元环配体形成了7个坐标的配合物，其中大环定义了近似五边形双锥体的赤道面，轴向位点被水分子或共价键占据。阴离子。N 3 X 2供体组的几何形状（X = O或S）以及因此对不同金属离子的拟合优劣主要取决于大环中苯环之间桥的性质。
• The chemistry of molybdenum and tungsten. Part XII. Molybdenum(V) and tungsten(V) complexes of nitrogen-sulphur chelating ligands. Facile amine deprotonations
  作者：C.A. McAuliffe、F.P. McCullough、A. Werfalli

  DOI：10.1016/s0020-1693(00)89627-9

  日期：1978.1

  ne, 1,3-di(o-aminobenzenethio)propane and 1,4-di(o-aminobenzenethio)butane react with MOCl3(THF)2 (M = Mo, W) to form the [MOCl1(ligand)]2 complexes in which the ligand is a zwitterion, having transferred a proton from one amine group to the other. The simpler o-aminobenzenethiol reacts with MoOCL3(THF)2 to form [MoOCl3(ligand)3]. E.p.r., infrared and electronic spectra, as well as magnetic moments

  摘要螯合配体1,2-二（邻氨基苯硫基）乙烷，顺式1,2,2-二（邻氨基苯硫基）乙烯，1,3-二（邻氨基苯硫基）丙烷和1,4-二（邻氨基）氨基苯硫基）丁烷与MOCl3（THF）2（M = Mo，W）反应形成[MOCl1（配体）] 2配合物，其中的配体为两性离子，已将质子从一个胺基转移到另一个胺基上。较简单的邻氨基苯硫醇与MoOCL3（THF）2反应形成[MoOCl3（配体）3]。讨论了Epr，红外和电子光谱，以及磁矩和电导率数据。
• Synthesis, spectroscopic and redox behaviour of copper(II), nickel(II) and cobalt(II) complexes of some macrocyclic multidentates
  作者：PR. Athappan、G. Rajagopal

  DOI：10.1016/0277-5387(95)00182-r

  日期：1996.2

  Copper(II) complexes of neutral tetradentate diamines and a series of copper(II), nickel(II) and cobalt(II) complexes of a new class of dibasic hexadentate Schiff bases, derived from the above diamines and salicylaldehyde or 2-hydroxy-1-naphthaldehyde, have been prepared and characterized by elemental analysis, magnetic susceptibility and IR and electronic spectral studies. The electrochemical behaviour

  中性四齿二胺的铜（II）配合物，以及由上述二胺和水杨醛或2-羟基-苯胺衍生的新型二元六齿席夫碱的一系列铜（II），镍（II）和钴（II）配合物已经制备了1-萘醛，并通过元素分析，磁化率以及红外光谱和电子光谱研究对其进行了表征。还研究了铜（II）和钴（II）配合物的电化学行为以及所有铜（II）配合物的ESR光谱参数。配体场强随螯合物环尺寸从六增加到七而增加。ESR光谱数据表明，铜（II）配合物呈现单体扭曲的八面体或拟四面体结构。乙腈中的II / Cu I和Co II / Co I对。