3-methyl-2-(2-(phenylthio)phenyl)pyridine | 1584673-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-2-(2-(phenylthio)phenyl)pyridine
• 英文别名: 3-Methyl-2-(2-phenylsulfanylphenyl)pyridine；3-methyl-2-(2-phenylsulfanylphenyl)pyridine
• CAS: 1584673-22-2
• 化学式: C₁₈H₁₅NS
• 分子量: 277.39
• InChiKey: GKUMYOYMFLHYDD-UHFFFAOYSA-N

物化性质

• 沸点：
  402.7±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯二硫醚 在 双(乙腈)氯化钯(II) 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 3-methyl-2-(2-(phenylthio)phenyl)pyridine
  参考文献：
  名称：

  Pd(II)-catalyzed selective sulfenylation of arene C–H bonds using N-arylthiobenzamides as thiolation reagent and oxidant

  摘要：

  The palladium-catalyzed direct sulfenylation of arenes with N-arylthiobenzamides was developed for the synthesis of aryl sulfides. Additional oxidant was not required for the catalytic cycle because N-arylthiobenzamide was used as both thiolation reagent and oxidant. The selective mono- or di-sulfenylation could be controlled by addition of the amount of N-arylthiobenzamide. Excellent functional group tolerance was observed and thioethers or dithioethers were obtained in good yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.077

文献信息

• Palladium-Catalyzed Direct Thiolation of Aryl CH Bonds with Disulfides
  作者：Masayuki Iwasaki、Miki Iyanaga、Yuta Tsuchiya、Yugo Nishimura、Wenjuan Li、Zhiping Li、Yasushi Nishihara

  DOI：10.1002/chem.201304717

  日期：2014.2.24

  A catalytic variant of the direct thiolation of arenes, bearing directing groups, with disulfides or thiols has been developed under palladium and copper co‐catalysis. Both sulfenyl moieties of the disulfide could be incorporated into the thiolated products, therefore, the reactions reached completion with only half an equivalent of disulfide, with respect to the starting arene. Experimental evidence

  在钯和铜的共催化下，开发了带有二价硫或硫醇的带有导向基团的芳烃直接硫醇化的催化变体。二硫化物的两个亚硫基部分都可以结合到硫醇化产物中，因此，相对于起始芳烃，仅用一半当量的二硫化物就可以完成反应。实验证据表明该反应是通过Pd II / Pd IV机制进行的。
• Rhodium-Catalyzed Directed Sulfenylation of Arene CH Bonds
  作者：Yaxi Yang、Wei Hou、Lihuai Qin、Juanjuan Du、Huijin Feng、Bing Zhou、Yuanchao Li

  DOI：10.1002/chem.201303730

  日期：2014.1.7

  The rhodium‐catalyzed intermolecular direct CH thiolation of arenes with aryl and alkyl disulfides was developed for the first time to provide a convenient route to aryl thioethers. This strategy is compatible with many different directing groups and exhibits excellent functional group tolerance. More significantly, mono‐ or dithiolation can be selectively achieved, thus providing a straightforward

  首次开发了铑催化芳烃和烷基二硫化物的分子间直接CH硫醇化反应，从而为制备芳基硫醚提供了便利的途径。该策略可与许多不同的导向基团兼容，并具有出色的官能团耐受性。更重要的是，可以选择性地实现单或二硫代化，从而为选择性制备芳基硫醚和二硫醚提供了直接的方法。
• Lewis Acid/Brønsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(<i>sp</i>²)–H Bonds with <i>N</i>-(Arylthio)i(a)mides
  作者：Manthena Chaitanya、Pazhamalai Anbarasan

  DOI：10.1021/acs.orglett.8b01281

  日期：2018.6.1

  C–H bonds have been accomplished employing N-(arylthio)imides in combination with either Brønsted acid or Lewis acid, respectively. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N–S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C–H bonds. A plausible

  使用N-（芳硫基）酰亚胺分别与Brønsted酸或Lewis酸结合使用，可实现高效的化学扩散的钯催化的硫键化（CS）和酰亚胺化（CN）。所开发方法的显着特征包括出色的多样性，高官能团耐受性，广泛的底物范围以及使用单个N-S试剂。重要的是，已发展的假设也成功地扩展到C–H键的酰胺化。在初步的机理研究的基础上，提出了一条可行的机理途径。
• The Palladium-Catalyzed Intermolecular C–H Chalcogenation of Arenes
  作者：Renhua Qiu、Vutukuri Prakash Reddy、Takanori Iwasaki、Nobuaki Kambe

  DOI：10.1021/jo502402d

  日期：2015.1.2

  Palladium catalyzes the intermolecular chalcogenation of carbazole, 2-phenylpyridine, benzo[h]quinolone, and indole derivatives with disulfides and diselenides via selective C-H bond cleavage, providing a convenient route to thio and selenoethers.
• Pd(II)-catalyzed selective sulfenylation of arene C–H bonds using N-arylthiobenzamides as thiolation reagent and oxidant
  作者：Xing-Song Zhang、Guoxing Li、Xing-Guo Zhang、Xiao-Hong Zhang

  DOI：10.1016/j.tet.2015.06.077

  日期：2015.8

  The palladium-catalyzed direct sulfenylation of arenes with N-arylthiobenzamides was developed for the synthesis of aryl sulfides. Additional oxidant was not required for the catalytic cycle because N-arylthiobenzamide was used as both thiolation reagent and oxidant. The selective mono- or di-sulfenylation could be controlled by addition of the amount of N-arylthiobenzamide. Excellent functional group tolerance was observed and thioethers or dithioethers were obtained in good yields. (C) 2015 Elsevier Ltd. All rights reserved.