2-(naphthalen-2-ylthio)aniline

• 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-(naphthalen-2-ylthio)aniline
• 英文别名: 2-Naphthalen-2-ylsulfanylaniline
• 化学式: C₁₆H₁₃NS
• mdl: MFCD12425142
• 分子量: 251.352
• InChiKey: YTRKJTLPWRRULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-ylthio)aniline 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 sodium t-butanolate 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 10-(naphthalen-1-yl)-10H-phenothiazine
  参考文献：
  名称：

  通过N-和S-芳基化序列的无过渡金属合成N-芳基吩噻嗪

  摘要：

  公开了在无过渡金属的条件下由邻-硫烷基苯胺合成N-芳基吩噻嗪的有效方法。邻硫烷基苯胺的N-和S-芳基化序列使我们能够合成各种N-芳基吩噻嗪。特别是，N-芳基吩噻嗪的一锅法合成是通过容易地获得的模块，通过对芳烃中间体进行硫胺化并按照N-和S-芳基化顺序制备邻-硫烷基苯胺来完成的。

  DOI：

  10.1021/acs.orglett.1c00515
• 作为产物：
  描述：

  (naphthalen-3-yl)(2-nitrophenyl)sulfane 在 钾硼氢 、 TPGS-750-M 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以92%的产率得到2-(naphthalen-2-ylthio)aniline
  参考文献：
  名称：

  掺有ppm级（Pd + Ni）的Fe纳米颗粒中的协同效应。可持续还原硝基的新催化剂

  摘要：

  在铁纳米颗粒中嵌入的Pd和Ni的ppm水平之间发现了显着的协同作用，这导致室温下水中的含硝基芳族化合物和杂芳族化合物温和选择性催化还原。NaBH 4用作廉价氢化物的来源。记录了广泛的基材范围以及其他一些功能，包括：催化剂用量低，产品中残留金属少，催化剂和反应介质的循环利用，凸显了这项新技术的绿色本质。

  DOI：

  10.1039/c7gc02991h

文献信息

• Metal-Free Iodine-Catalyzed Direct Arylthiation of Substituted Anilines with Thiols
  作者：Daoshan Yang、Kelu Yan、Wei Wei、Jing Zhao、Mengqi Zhang、Xuguang Sheng、Guoqing Li、Shenglei Lu、Hua Wang

  DOI：10.1021/acs.joc.5b00540

  日期：2015.6.19

  Iodine-catalyzed direct arylthiation of substituted anilines for the synthesis of various diaryl sulfides has been developed under metal- and solvent-free conditions. The present method uses readily available thiols as the arylthiation reagents, and environmentally friendly and inexpensive I-2 as the catalyst. Importantly, no base or ligand was necessary. Such a simple, efficient, and economical transformation provides an attractive approach to various diaryl sulfides in good to excellent yields.
• 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.
• Davies et al., Journal of the Chemical Society, 1952, p. 4678,4681
  作者：Davies et al.

  DOI：——

  日期：——
• Synergistic effects in Fe nanoparticles doped with ppm levels of (Pd + Ni). A new catalyst for sustainable nitro group reductions
  作者：Haobo Pang、Fabrice Gallou、Hyuntae Sohn、Jeffrey Camacho-Bunquin、Massimiliano Delferro、Bruce H. Lipshutz

  DOI：10.1039/c7gc02991h

  日期：——

  A remarkable synergistic effect has been uncovered between ppm levels of Pd and Ni embedded within iron nanoparticles that leads to mild and selective catalytic reductions of nitro-containing aromatics and heteroaromatics in water at room temperature. NaBH4 serves as the source of inexpensive hydride. Broad substrate scope is documented, along with several other features including: low catalyst loading

  在铁纳米颗粒中嵌入的Pd和Ni的ppm水平之间发现了显着的协同作用，这导致室温下水中的含硝基芳族化合物和杂芳族化合物温和选择性催化还原。NaBH 4用作廉价氢化物的来源。记录了广泛的基材范围以及其他一些功能，包括：催化剂用量低，产品中残留金属少，催化剂和反应介质的循环利用，凸显了这项新技术的绿色本质。
• Transition-Metal-Free Synthesis of <i>N-</i>Arylphenothiazines through an <i>N</i>- and <i>S</i>-Arylation Sequence
  作者：Tsubasa Matsuzawa、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1021/acs.orglett.1c00515

  日期：2021.3.19

  transition-metal-free conditions is disclosed. An N- and S-arylation sequence of o-sulfanylanilines enabled us to synthesize a wide variety of N-arylphenothiazines. In particular, one-pot synthesis of N-arylphenothiazines was accomplished from easily available modules through preparation of o-sulfanylanilines by thioamination of aryne intermediates and following N- and S-arylation sequence.

  公开了在无过渡金属的条件下由邻-硫烷基苯胺合成N-芳基吩噻嗪的有效方法。邻硫烷基苯胺的N-和S-芳基化序列使我们能够合成各种N-芳基吩噻嗪。特别是，N-芳基吩噻嗪的一锅法合成是通过容易地获得的模块，通过对芳烃中间体进行硫胺化并按照N-和S-芳基化顺序制备邻-硫烷基苯胺来完成的。