2-((2-chlorophenyl)thio)benzonitrile

• 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-((2-chlorophenyl)thio)benzonitrile
• 英文别名: 2-(2-Chlorophenyl)sulfanylbenzonitrile
• 化学式: C₁₃H₈ClNS
• mdl: MFCD11124194
• 分子量: 245.732
• InChiKey: ZUHMPLJSDJTSSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻氯苯硫酚 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 、 potassium carbonate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 13.0h， 生成 2-((2-chlorophenyl)thio)benzonitrile
  参考文献：
  名称：

  连续的 C-H 活化能够方便地传递多功能芳烃

  摘要：

  从丰富的原料中模块化构建多功能芳烃是合成化学的不懈追求，加速了药物和材料的发现。在此，使用多功能亚胺酸酯的多重 C-H 活化策略，实现了密集功能化的含硫芳烃分子库的便捷传递，从而能够简明地构建生物活性分子，如双苯萘酚。

  DOI：

  10.1039/d1cc03243g

文献信息

• Facile synthesis of 1,2-thiobenzonitriles <i>via</i> Cu-catalyzed denitrogenative radical coupling reaction
  作者：Yao Zhou、Ya Wang、Yixian Lou、Qiuling Song

  DOI：10.1039/c9cc05099j

  日期：——

  A Cu-catalyzed synthesis of 1,2-thiobenzonitriles via oxidative C–N cleavage of 3-aminoindazoles followed by radical coupling with thiols is developed. A diverse array of 1,2-thiobenzonitriles were obtained in good yields with wide substrate scope. Notably, this is the first example of denitrogenative radical coupling with 3-aminoindazoles.

  的Cu-催化的1,2- thiobenzonitriles合成通过3- aminoindazoles接着用硫醇自由基偶合的氧化C-N裂解显影。以良好的收率和宽的底物范围获得了各种各样的1,2-硫代苄腈。值得注意的是，这是脱氮自由基与3-氨基吲唑偶联​​的第一个例子。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
• Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6
  作者：Elisabeth A. Schmittling、J. Scott Sawyer

  DOI：10.1021/jo00064a004

  日期：1993.6

  An efficient alternative to the copper-catalyzed synthesis (Ullmann ether synthesis) of diaryl ethers, diaryl thioethers, and diarylamines involving the potassium fluoride-alumina-mediated addition of a phenol, thiophenol, or an aniline to 2- or 4-fluorobenzonitriles catalyzed by 18-crown-6 is described.
• Sequential C–H activation enabled expedient delivery of polyfunctional arenes
  作者：Wensen Ouyang、Xiaoqing Cai、Xiaojian Chen、Jie Wang、Jianhang Rao、Yang Gao、Yanping Huo、Qian Chen、Xianwei Li

  DOI：10.1039/d1cc03243g

  日期：——

  Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C–H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction

  从丰富的原料中模块化构建多功能芳烃是合成化学的不懈追求，加速了药物和材料的发现。在此，使用多功能亚胺酸酯的多重 C-H 活化策略，实现了密集功能化的含硫芳烃分子库的便捷传递，从而能够简明地构建生物活性分子，如双苯萘酚。