N,N-diallyl-4-phenylthioaniline

• 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-diallyl-4-phenylthioaniline
• 英文别名: 4-phenylsulfanyl-N,N-bis(prop-2-enyl)aniline
• 化学式: C₁₈H₁₉NS
• 分子量: 281.422
• InChiKey: RDHICBLWWULQRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-diallyl-4-phenylthioaniline 、 4-甲氧基苯酚 在 naphthalene-1,8-diylbis(diphenylmethylium) diperchlorate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以86%的产率得到4-diallylaminophenyl 4-methoxyphenyl 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-diallyl-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

文献信息

• 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.