triethylammonium o-bromophenyl dithiocarbamate salt | 58654-89-0

• 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: triethylammonium o-bromophenyl dithiocarbamate salt
• CAS: 58654-89-0
• 化学式: C₆H₁₅N*C₇H₆BrNS₂
• 分子量: 349.359
• InChiKey: SSGOROLKHSOKFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  15.27
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  triethylammonium o-bromophenyl dithiocarbamate salt 在 吡啶 、 三光气 作用下， 以 氯仿 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

  摘要：

  DOI：

  10.1016/j.bmc.2021.116265
• 作为产物：
  描述：

  二硫化碳 、 三乙胺 、 2-溴苯胺 生成 triethylammonium o-bromophenyl dithiocarbamate salt
  参考文献：
  名称：

  一锅制备 氰胺 使用分子碘从二硫代氨基甲酸酯中提取

  摘要：

  公开了一种通过使用分子碘的双脱硫策略由二硫代氨基甲酸盐合成氰胺的有效的一锅法。二硫代氨基甲酸酯，通过碘的作用异硫氰酸酯 原位，经水处理NH 3 给 硫脲。这硫脲因此生成的产物经I 2进一步氧化脱硫，从而以良好的收率得到相应的氰酰胺。环境友好性，成本效益和高产量是这一一锅法的重要属性。

  DOI：

  10.1039/b914283p

文献信息

• Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides
  作者：Tian-Tian Li、Xiang-Hai Song、Mei-Shuang Wang、Ning Ma

  DOI：10.1039/c4ra04628e

  日期：——

  Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2 served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

  多种二取代和三取代硫脲通过二硫代氨基甲酸TEA（或DABCO）盐与胺在室温下使用硝酸铈铵（CAN）作为催化剂进行缩合反应，以高产率合成。这是一种一步法，无需分离异硫氰酸酯。该反应可能涉及胺对异硫氰酸酯的亲核加成，异硫氰酸酯是由二硫代氨基甲酸盐的氧化偶联以及随后双(氨基硫羰基)二硫化物的分解产生的。当使用二级胺和CS2作为反应物时，通过串联的亲核加成/氧化偶联反应，以中等至优异的产率获得了双(氨基硫羰基)二硫化物。在所有偶联反应中，氧化剂为空气，CAN可能作为单电子转移催化剂发挥作用。
• Slight structural modulation around a pivotal bond: high impact on enantiomeric stability
  作者：Daniel Farran、Nicolas Vanthuyne、Giulia Bossa、Vincent Belot、Muriel Albalat、Marion Jean、Christian Roussel

  DOI：10.1039/d1nj03178c

  日期：——

  robust to be handled without risk of racemization) and 13 stable atropisomers. The influence of the flanking substituents was investigated showing that a minor structural modification may result in a drastic change on the value of the rotational barrier. All these results offer a set data on structure-rotational barrier relationships very helpful to design molecules exhibiting chiral axis or to optimize

  基于N-芳基噻唑啉支架，合成了22 个具有 N-C芳基手性轴的结构，在关键键周围的四个侧翼取代基表现出巨大的分子多样性。通过热动力学实验或从平台形状手性 HPLC 色谱图的分析确定它们相应的旋转障碍，允许根据它们的对映体稳定性对这些化合物进行排序：4 个旋转异构体，5 个可分离的阻转异构体（即不够坚固，无法在没有外消旋化风险的情况下进行处理）和 13 种稳定的阻转异构体。研究了侧翼取代基的影响，表明微小的结构修改可能导致旋转势垒值的急剧变化。所有这些结果提供了一组关于结构-旋转势垒关系的数据，非常有助于设计具有手性轴的分子或优化这种结构的对映体稳定性。为了完成这项研究，通过 X 射线分析和 DFT 计算检查了外消旋化途径，突出了过渡态期间芳环畸变对旋转能量成本的重要性。
• Copper(I)-Catalyzed Cascade Synthesis of 2-Substituted 1,3-Benzothiazoles: Direct Access to Benzothiazolones
  作者：Siva Murru、Pravat Mondal、Ramesh Yella、Bhisma K. Patel

  DOI：10.1002/ejoc.200900711

  日期：2009.11

  An efficient cascade process for the preparation of 2-substituted 1,3-benzothiazoles directly from 2-haloaryl isothiocyanates and O or S nucleophiles by a Cu-catalyzed, intramolecular, C–S bond formation has been developed. This cascade method is viable for the efficient syntheses of both O- and S-substituted 1,3-benzothiazoles. Furthermore, 1,3-benzothiazol-2(3H)-ones having an alkyl group allow easy

  已经开发出一种通过 Cu 催化的分子内 C-S 键形成直接从 2-卤代芳基异硫氰酸酯和 O 或 S 亲核试剂制备 2-取代 1,3-苯并噻唑的高效级联工艺。这种级联方法对于 O-和 S-取代的 1,3-苯并噻唑的有效合成是可行的。此外，具有烷基的 1,3-苯并噻唑-2(3H)-酮易于获得 1,3-苯并噻唑酮。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Axially chiral N-(o-aryl)-2-thioxo-oxazolidine-4-one and rhodanine derivatives: enantiomeric separation and determination of racemization barriers
  作者：Esra Müjde Yılmaz、İlknur Doğan

  DOI：10.1016/j.tetasy.2008.09.001

  日期：2008.9

  Axially chiral 5,5-dimethyl-3-(o-aryl)rhodanine, 3-(o-aryl)rhodanine and 5,5-dimethyl-3-(o-aryl)-2-thioxo-4-oxazolidinone derivatives have been synthesized as racemates and the energy barriers to enantiomerization have been determined by dynamic H-1 NMR or by following the thermal equilibration of the separated enantiomers using chiral HPLC. The barriers to rotation about the N-sp2-C-aryl single bond were found to be 82-129 kJ/mol. The racemization barriers in these compounds are affected by the size of the ortho-substituent on the aryl ring. The magnitude of the barriers was found to change linearly with the van der Waals radii of the ortho-halogen substituents. (C) 2008 Elsevier Ltd. All Fights reserved.
• Intra- and Intermolecular C−S Bond Formation Using a Single Catalytic System: First Direct Access to Arylthiobenzothiazoles
  作者：Siva Murru、Harisadhan Ghosh、Santosh K. Sahoo、Bhisma K. Patel

  DOI：10.1021/ol9017535

  日期：2009.10.1

  We have for the first time developed two ligand-assisted Cu(I)-catalyzed sequential intra- and intermolecular Sarylations leading to the direct synthesis of arylthiobenzothiazoles in one pot without an inert atmosphere. Low catalyst loading, inexpensive metal catalyst and ligand, lower reaction temperature, and shorter reaction times make this method superior to all reported methods for the synthesis of arylthiobenzothiazole.