2-((4-methoxyphenyl)thio)-5-(trifluoromethyl)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-((4-methoxyphenyl)thio)-5-(trifluoromethyl)benzonitrile
• 英文别名: 2-[(4-Methoxyphenyl)sulfanyl]-5-(trifluoromethyl)benzenecarbonitrile；2-(4-methoxyphenyl)sulfanyl-5-(trifluoromethyl)benzonitrile
• 化学式: C₁₅H₁₀F₃NOS
• 分子量: 309.312
• InChiKey: MWBAAKWAOCRHID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二乙基硫代膦酰-二乙基-硫代膦烷 、 2-((4-methoxyphenyl)thio)-5-(trifluoromethyl)benzonitrile 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 1,2-bis[bis(4-methoxyphenyl)phosphanyl]ethane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到4-methoxyphenyl diethyldithiophosphinate
  参考文献：
  名称：

  铑催化杂芳基硫化物的膦酰化反应合成二烷基（杂芳基）膦硫化物

  摘要：

  二烷基（杂芳基）膦硫化物是通过杂芳基芳基硫化物和四烷基二膦二硫化物的铑催化交换反应合成的。该反应具有广泛的适用性，可得到包含五元和六元杂芳基的各种二烷基（杂芳基）膦硫化物。通过脱硫获得各种二烷基（杂芳基）膦。

  DOI：

  10.1002/adsc.201800630
• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 2-氯-5-三氟甲基苯腈 在 potassium fluoride on basic alumina 、 18-冠醚-6 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以88%的产率得到2-((4-methoxyphenyl)thio)-5-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹

  摘要：

  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.

  DOI：

  10.1021/jo980800g

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。