O-(2,2-dimethylpropyl) [2-(N-tert-butyl-2,6-dichloroanilino)-2-oxoethyl]sulfanylmethanethioate | 864365-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-(2,2-dimethylpropyl) [2-(N-tert-butyl-2,6-dichloroanilino)-2-oxoethyl]sulfanylmethanethioate
• CAS: 864365-03-7
• 化学式: C₁₈H₂₅Cl₂NO₂S₂
• 分子量: 422.44
• InChiKey: BWYJQYRLHICTFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-(2,2-dimethylpropyl) [2-(N-tert-butyl-2,6-dichloroanilino)-2-oxoethyl]sulfanylmethanethioate 在 过氧化双月桂酰 作用下， 以 氯苯 为溶剂， 以26%的产率得到1,3-二氯-2-[2-(2,6-二氯苯基)乙基]苯
  参考文献：
  名称：

  An Unusual Radical Smiles Rearrangement

  摘要：

  Radicals derived from N-(alpha-xanthyl)acetanilides or N-(alpha-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.

  DOI：

  10.1021/ol051568l
• 作为产物：
  描述：

  2,6-二氯苯胺 在 三氟化硼乙醚 、 N,N-二甲基苯胺 作用下， 以 环己烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.0h， 生成 O-(2,2-dimethylpropyl) [2-(N-tert-butyl-2,6-dichloroanilino)-2-oxoethyl]sulfanylmethanethioate
  参考文献：
  名称：

  An Unusual Radical Smiles Rearrangement

  摘要：

  Radicals derived from N-(alpha-xanthyl)acetanilides or N-(alpha-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.

  DOI：

  10.1021/ol051568l

文献信息

• An Unusual Radical Smiles Rearrangement
  作者：Eric Bacqué、Myriem El Qacemi、Samir Z. Zard

  DOI：10.1021/ol051568l

  日期：2005.8.1

  Radicals derived from N-(alpha-xanthyl)acetanilides or N-(alpha-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.