N,N-diethyl-4-phenylthioaniline | 862175-98-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N,N-diethyl-4-phenylthioaniline
• 英文别名: N,N-diethyl-4-phenylsulfanylaniline
• CAS: 862175-98-2
• 化学式: C₁₆H₁₉NS
• 分子量: 257.4
• InChiKey: JKUIKQKGPQPEKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  68-69 °C(Solv: ethanol (64-17-5))
• 沸点：
  400.5±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-4-phenylthioaniline 、 2,4,6-三甲酚 在 naphthalene-1,8-diylbis(diphenylmethylium) diperchlorate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以73%的产率得到4-diethylaminophenyl 2,4,6-trimethylphenyl ether
  参考文献：
  名称：

  Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis:  Oxidative Arylation of Phenols with N,N-Dialkyl-4-phenylthioanilines

  摘要：

  Various aryl 4-dialkylaminophenyl ethers were readily synthesized without heating in good yield from phenols and N,N-dialkyl-4-phenylthioanilines. This oxidative arylation of phenols was successfully promoted by a bis(diphenylmethylium)naphthalenediyl dication via ipso-substitution of the phenylthio group in the anilines through a radical process.

  DOI：

  10.1021/ja051839n
• 作为产物：
  描述：

  4-溴苯胺 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.5h， 生成 N,N-diethyl-4-phenylthioaniline
  参考文献：
  名称：

  Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis:  Oxidative Arylation of Phenols with N,N-Dialkyl-4-phenylthioanilines

  摘要：

  Various aryl 4-dialkylaminophenyl ethers were readily synthesized without heating in good yield from phenols and N,N-dialkyl-4-phenylthioanilines. This oxidative arylation of phenols was successfully promoted by a bis(diphenylmethylium)naphthalenediyl dication via ipso-substitution of the phenylthio group in the anilines through a radical process.

  DOI：

  10.1021/ja051839n
• 作为试剂：
  描述：

  naphthalene-1,8-diylbis(diphenylmethylium) diperchlorate 在 N,N-diethyl-4-phenylthioaniline 、 N,N-diethyl-4-(tributylstannyl)aniline 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到1,1,2,2-tetraphenylacenaphthene
  参考文献：
  名称：

  Naphthalene-1,8-diylbis(diphenylmethylium) 介导的氧化芳基化：三芳基锍盐的合成路线

  摘要：

  双阳离子物质，萘-1,8-二基双（二苯基甲基鎓），成功地促进了（4-N,N-二烷基氨基苯基）苯基硫化物中硫原子与（4-N,N-二烷基氨基苯基）硅烷的氧化芳基化，得到了三芳基锍盐良好的产量。

  DOI：

  10.1246/cl.2010.56

文献信息

• Iodine/Sulfinates: Rapid and Convenient Thiolation of Imidazo Heterocycles without Additives
  作者：Sébastien Redon、Patrice Vanelle、Anne-Sophie Mendes

  DOI：10.1055/a-2043-4740

  日期：——

  An unprecedented I2/sulfinate thiolating system is described for the sulfenylation of electron-rich heterocycles. This phosphine-free strategy permits simple, efficient, and fast sulfenylation of imidazo heterocycles, anilines, indoles, coumarins, or enaminones.

  摘要 描述了一种前所未有的 I2/硫酸硫醇化系统，用于富电子杂环的亚硒化。这种不含磷化氢的方法可以简单、高效、快速地对咪唑杂环、苯胺、吲哚、香豆素或烯丙酮进行亚硒化反应。
• Oxidative Arylation Mediated by Naphthalene-1,8-diylbis(diphenylmethylium): Synthetic Route to Triarylsulfonium Salts
  作者：Hiroyuki Tanabe、Takaharu Kawai、Terunobu Saitoh、Junji Ichikawa

  DOI：10.1246/cl.2010.56

  日期：2010.1.5

  naphthalene-1,8-diylbis(diphenylmethylium), successfully promoted oxidative arylation of the sulfur atom in (4-N,N-dialkylaminophenyl) phenyl sulfides with (4-N,N-dialkylaminopheny)silanes, affording triarylsulfonium salts in good yield.

  双阳离子物质，萘-1,8-二基双（二苯基甲基鎓），成功地促进了（4-N,N-二烷基氨基苯基）苯基硫化物中硫原子与（4-N,N-二烷基氨基苯基）硅烷的氧化芳基化，得到了三芳基锍盐良好的产量。
• Bis(triarylmethylium)-Mediated Diaryl Ether Synthesis:  Oxidative Arylation of Phenols with <i>N</i>,<i>N</i>-Dialkyl-4-phenylthioanilines
  作者：Terunobu Saitoh、Junji Ichikawa

  DOI：10.1021/ja051839n

  日期：2005.7.13

  Various aryl 4-dialkylaminophenyl ethers were readily synthesized without heating in good yield from phenols and N,N-dialkyl-4-phenylthioanilines. This oxidative arylation of phenols was successfully promoted by a bis(diphenylmethylium)naphthalenediyl dication via ipso-substitution of the phenylthio group in the anilines through a radical process.