2-((4-(trifluoromethyl)phenyl)thio)aniline | 872513-57-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((4-(trifluoromethyl)phenyl)thio)aniline
• 英文别名: 2-{[4-(Trifluoromethyl)phenyl]sulfanyl}aniline；2-[4-(trifluoromethyl)phenyl]sulfanylaniline
• CAS: 872513-57-0
• 化学式: C₁₃H₁₀F₃NS
• 分子量: 269.29
• InChiKey: BASREWUSAPEZEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((4-(trifluoromethyl)phenyl)thio)aniline 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-((4-(trifluoromethyl)phenyl)thio)phenyl)pivalamide
  参考文献：
  名称：

  钯催化的酰胺的C（羰基）–C键裂解：醇类很容易获得氨基甲酸苯酯衍生物†

  摘要：

  据报道，含硫的助剂可以使钯催化的酰胺的C（羰基）–C键活化，与醇形成苯基氨基甲酸酯衍生物。烷基醇和苄醇都可以很好地使用，产率高达85％。从苯基氨基甲酸酯到脲和硫代氨基甲酸酯的衍生物说明了这种连续的C–C裂解/ C–O偶联反应的潜在应用。

  DOI：

  10.1039/c8cc03954b
• 作为产物：
  描述：

  苯并噻唑 、 对溴三氟甲苯 在 lithium tert-butoxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 24.0h， 以17%的产率得到2-((4-(trifluoromethyl)phenyl)thio)aniline
  参考文献：
  名称：

  Heterogeneous Copper–Catalyzed Synthesis of S–Arylated 2-Aminothiophenols via Ring Opening of Benzothiazoles and C–S Coupling using Aryl Halides

  摘要：

  Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl iodides or aryl bromides in the presence of lithium tert-butoxide in aqueous 2-propanol.

  DOI：

  10.3987/com-18-s(t)55

文献信息

• Tipping the Balance between S-π and O-π Interactions
  作者：Jungwun Hwang、Ping Li、Mark D. Smith、Constance E. Warden、Dominic A. Sirianni、Erik C. Vik、Josef M. Maier、Christopher J. Yehl、C. David Sherrill、Ken D. Shimizu

  DOI：10.1021/jacs.8b07617

  日期：2018.10.17

  comprehensive experimental survey consisting of 36 molecular balances was conducted to compare 18 pairs of S-π versus O-π interactions over a wide range of structural, geometric, and solvent parameters. A strong linear correlation was observed between the folding energies of the sulfur and oxygen balances across the entire library of balance pairs. The more stable interaction systematically switched

  进行了由 36 个分子平衡组成的综合实验调查，以在广泛的结构、几何和溶剂参数范围内比较 18 对 S-π 与 O-π 相互作用。在整个平衡对库中硫和氧平衡的折叠能之间观察到很强的线性相关性。更稳定的相互作用系统地从 O-π 转换为 S-π 相互作用。双分子PhSCH3-芳烃和PhOCH3-芳烃复合物的计算研究能够复制分子平衡的实验趋势。O-π 到 S-π 相互作用的偏好变化是由于稳定（分散和疏溶剂）和不稳定（交换排斥）术语的相互作用，这是由于氧和硫原子的大小和极化率的差异引起的。
• Copper-promoted <i>S</i>-arylation reactions with triarylbismuths for the synthesis of diaryl sulfides
  作者：Mei Nie、Xuehao Zhou、Jingjie Tang、Dongting Huang、Xinsheng Xiao、Jianwei Xie

  DOI：10.1039/d3ra06582k

  日期：——

  A simple approach for copper-promoted S-arylation reactions utilizing triarylbismuths or triarylantimonys as arylating reagents has been described. These reactions can be performed under mild conditions and exhibit remarkable functional group tolerance and chemoselectivity. The corresponding 2-arylthiopyridine 1-oxide derivatives and arylthioanilines/phenols have been successfully synthesized, achieving

  已经描述了利用三芳基铋或三芳基锑作为芳基化试剂的铜促进的S-芳基化反应的简单方法。这些反应可以在温和的条件下进行，并表现出显着的官能团耐受性和化学选择性。相应的 2-芳硫基吡啶 1-氧化物衍生物和芳硫基苯胺/苯酚已成功合成，在超过 49 个实例中实现了良好至优异的产率。
• A convenient and efficient copper-catalyzed synthesis of unsymmetrical and symmetrical diaryl chalcogenides from arylboronic acids in ethanol at room temperature
  作者：Amit Kumar、Sangit Kumar

  DOI：10.1016/j.tet.2014.01.030

  日期：2014.3

  A simple and convenient approach for the synthesis of unsymmetrical diaryl chalcogenides (Te, Se, and S) has been developed by copper-catalyzed cross-coupling reaction of organoboronic acid with diaryl dichalcogenide in ethanol using NaBH4 in air or oxygen. The present methodology is highly practical for the synthesis of unsymmetrical diaryl tellurides with various functionalities such as -NO2, -F, -Br, and -COOH that have been obtained in good to excellent yields. Methodology is also effective for the synthesis of unsymmetrical diaryl selenides and sulfides. Moreover, symmetrical diaryl selenides have also been obtained from arylboronic acids using elemental selenium powder under optimized reaction conditions. The use of NaBH4 is the key for the development of milder reaction conditions, which enable the construction of unsymmetrical diaryl chalcogenides from boronic acid substrates in ethanol at room temperature. (C) 2014 Elsevier Ltd. All rights reserved.