{2-methyl-6-[(4-tolyl)sulfanyl]pyridinium-1-yl}(4-tolyl)imide | 1346177-74-9

• 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-methyl-6-[(4-tolyl)sulfanyl]pyridinium-1-yl}(4-tolyl)imide
• 英文别名: [2-Methyl-6-(4-methylphenyl)sulfanylpyridin-1-ium-1-yl]-(4-methylphenyl)azanide
• CAS: 1346177-74-9
• 化学式: C₂₀H₂₀N₂S
• 分子量: 320.458
• InChiKey: QJLAZTRUESWMFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  {2-methyl-6-[(4-tolyl)sulfanyl]pyridinium-1-yl}(4-tolyl)imide 、 二苯乙烯酮 在 二氯甲烷 作用下， 反应 168.0h， 以21%的产率得到6-methyl-10-oxo-11,11-diphenyl-4,4a,10,11-tetrahydro-9H-9-aza-11b-azoniabenzo[de]fluorene chloride
  参考文献：
  名称：

  Transformation of Zwitterionic Pyridine Derivatives to a Spiro-Fused Ring System: Azoniabenzo[de]fluorine. Synthesis and Mechanistic Rationalization

  摘要：

  Reaction of aryl- and benzylsulfanopyridinium amidates bearing a methyl group in position 6 with 2 equiv of diphenylketene afforded a spiro-fused ring system: azoniabenzo[de]fluorine. By use of an excess amount of ketene, a distinct reaction was observed via which a 1H-pyrrolo[3,2-b]pyridin-2(3H)-one derivative was furnished. The structure of the tetracyclic spiro-fused ring system was unambiguously confirmed by X-ray diffraction, and its formation was rationalized by DFT calculations.

  DOI：

  10.1021/jo5022663

文献信息

• Rearrangement of Aryl- and Benzylthiopyridinium Imides with Participation of a Methyl Substituent
  作者：Roberta Palkó、Orsolya Egyed、Zsuzsanna Riedl、Tibor András Rokob、György Hajós

  DOI：10.1021/jo201645t

  日期：2011.11.18

  substituted 2-aryl- and 2-benzylthiopyridinium N-imides reacted with an excess of isocyanates to give N,N-disubstituted exocyclic1H-imidazo[4,5-b]pyridin-2(3H)-ones. The products easily underwent spontaneous [1,5] hydrogen shift to provide the heteroaromatic imidazopyridinone isomers. The transformation implied the initial formation of [1,2,4]triazolo[2,3-a]pyridinium salt, followed by deprotonation and

  6-甲基取代的2-芳基-和2-苄基硫代吡啶鎓N-酰亚胺与过量的异氰酸酯反应，得到N，N-二取代的环外环1 H-咪唑并[4，5 - b ]吡啶-2-2 （3 H）-。产物容易发生自发的[1,5]氢转移，以提供杂芳族咪唑并吡啶酮酮异构体。该转化表明[1,2,4]三唑[2,3- a ]的初始形成吡啶鎓盐，然后进行亚甲基部分的去质子化和氨基甲酰化，最后按照[1,3]σ型进行重排。机理上的考虑表明，一些实验发现揭示了环转化步骤的非一致的两步机理。
• Transformation of Zwitterionic Pyridine Derivatives to a Spiro-Fused Ring System: Azoniabenzo[<i>de</i>]fluorine. Synthesis and Mechanistic Rationalization
  作者：Roberta Palkó、Orsolya Egyed、Tibor András Rokob、Petra Bombicz、Zsuzsanna Riedl、György Hajós

  DOI：10.1021/jo5022663

  日期：2015.1.2

  Reaction of aryl- and benzylsulfanopyridinium amidates bearing a methyl group in position 6 with 2 equiv of diphenylketene afforded a spiro-fused ring system: azoniabenzo[de]fluorine. By use of an excess amount of ketene, a distinct reaction was observed via which a 1H-pyrrolo[3,2-b]pyridin-2(3H)-one derivative was furnished. The structure of the tetracyclic spiro-fused ring system was unambiguously confirmed by X-ray diffraction, and its formation was rationalized by DFT calculations.