N-(4'-p-tolylthio-2'-butynyl)-p-toluidine | 72248-80-7

• 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-(4'-p-tolylthio-2'-butynyl)-p-toluidine
• 英文别名: 4-methyl-N-[4-(4-methylphenyl)sulfanylbut-2-ynyl]aniline
• CAS: 72248-80-7
• 化学式: C₁₈H₁₉NS
• 分子量: 281.422
• InChiKey: HYUHHZQUATVETQ-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  451.8±40.0 °C(Predicted)
• 密度：
  1.11±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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4'-p-tolylthio-2'-butynyl)-p-toluidine 、 1-(4'-chlorobenzenesulfonyl)-4-chloro-2-butyne 在 magnesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.5h， 以39%的产率得到[4-(4-Chloro-benzenesulfonyl)-but-2-ynyl]-p-tolyl-(4-p-tolylsulfanyl-but-2-ynyl)-amine
  参考文献：
  名称：

  Mass spectral rearrangements of 3-arylsulphonyl-2-arylthiopropenes andN-(4′-arylsulphonyl-2′-butynyl)-N-(4″-arylthio-2″-butynyl)anilines

  摘要：

  AbstractUnder electron impact the title compounds undergo skeletal rearrangement in addition to the anticipated modes of cleavage. The 3‐arylsulphonyl‐2‐arylthiopropenes readily eliminate sulphur dioxide. Other modes of fragmentation include rearrangement to a bisaryl sulphide moiety and sulphone‐sulphinate rearrangement. The formation of a bisaryl sulphide ion is analogous to the behaviour of the isomeric trans‐1‐arylsulphonyl‐2‐arylthiopropenes. N‐(4′‐Arylsulphonyl‐2′‐butynyl)‐N‐(4″‐arylthio‐2″‐butynyl) anilines do not undergo any of the skeletal rearrangements mentioned above, but display the concerted loss of the arylsulphonyl and arylthio moieties. Similar eliminations have been observed from the analogous bis‐sulphides and bis‐sulphones.

  DOI：

  10.1002/oms.1210200404
• 作为产物：
  描述：

  乙烷,三氯氟- 、 1-(4-chlorobut-2-ynylsulfanyl)-4-methylbenzene 在 magnesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 N-(4'-p-tolylthio-2'-butynyl)-p-toluidine
  参考文献：
  名称：

  Mass spectral rearrangements of 3-arylsulphonyl-2-arylthiopropenes andN-(4′-arylsulphonyl-2′-butynyl)-N-(4″-arylthio-2″-butynyl)anilines

  摘要：

  AbstractUnder electron impact the title compounds undergo skeletal rearrangement in addition to the anticipated modes of cleavage. The 3‐arylsulphonyl‐2‐arylthiopropenes readily eliminate sulphur dioxide. Other modes of fragmentation include rearrangement to a bisaryl sulphide moiety and sulphone‐sulphinate rearrangement. The formation of a bisaryl sulphide ion is analogous to the behaviour of the isomeric trans‐1‐arylsulphonyl‐2‐arylthiopropenes. N‐(4′‐Arylsulphonyl‐2′‐butynyl)‐N‐(4″‐arylthio‐2″‐butynyl) anilines do not undergo any of the skeletal rearrangements mentioned above, but display the concerted loss of the arylsulphonyl and arylthio moieties. Similar eliminations have been observed from the analogous bis‐sulphides and bis‐sulphones.

  DOI：

  10.1002/oms.1210200404

文献信息

• Mass spectral rearrangements ofN-(4′-arylthio-2′-butynyl)N-(2″-arylthio-2″-propenyl)-p-toluidines,N,N-bis(2′-arylthio-2′-propenyl)-p-toluidines and 1,2-bis(arylthio)acenaphthenes
  作者：P. E. Glaspy、R. A. Hancock、B. S. Thyagarajan

  DOI：10.1002/oms.1210200312

  日期：1985.3

  AbstractUnder electron impact the title compounds display, in addition to the sequential loss of the arylthio groups, the elimination of a bisaryl disulphide moiety, but they do not eliminate sulphur. The behaviour of the p‐toluidine derivatives supports the rearrangement pathway proposed earlier for N,N‐bis(4′‐arylthio‐2′‐butynyl)anilines.