1-methyl-2-(methylthio)-4,5,6,7-tetrahydroazepine | 25355-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 1-methyl-2-(methylthio)-4,5,6,7-tetrahydroazepine
• 英文别名: 4,5,6,7-tetrahydro-1-methyl-2-(methylthio)azepine；1-methyl-7-methylsulfanyl-2,3,4,5-tetrahydro-1H-azepine；7-Methylmercapto-1-methyl-2,3,4,5-tetrahydro-1H-azepin；1-Methyl-2-methylmercapto-3,4,5,6-tetrahydro-azepin；1-Methyl-2-methylmercapto-3,4,5,6-tetrahydroazepin；1H-Azepine, 2,3,4,5-tetrahydro-1-methyl-7-(methylthio)-；1-methyl-7-methylsulfanyl-2,3,4,5-tetrahydroazepine
• CAS: 25355-54-8
• 化学式: C₈H₁₅NS
• 分子量: 157.28
• InChiKey: ZCDCAJNQYGAMLT-UHFFFAOYSA-N

物化性质

• 沸点：
  259.4±30.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-methyl-2-(methylthio)-4,5,6,7-tetrahydroazepine 以 乙醚 、 甲苯 为溶剂， 生成 1,3-Bis-(4-chloro-phenyl)-9-methyl-1,5,6,7,8,9-hexahydro-pyrimido[4,5-b]azepine-2,4-dione
  参考文献：
  名称：

  Takahata, Hiroki; Nakano, Masaharu; Tomiguhi, Akira, Heterocycles, 1982, vol. 17, p. 413 - 416

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基己内酰胺 在 劳森试剂 、 potassium tert-butylate 作用下， 生成 1-methyl-2-(methylthio)-4,5,6,7-tetrahydroazepine
  参考文献：
  名称：

  Coupling-Isomerization−N,S-Ketene Acetal-Addition SequencesA Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-b]azepines

  摘要：

  Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.

  DOI：

  10.1021/jo0602726

文献信息

• Activated lactams. VI. The cycloaddition reaction of cyclic ketene-S,N-acetals with dimethyl acetylenedicarboxylate.
  作者：HIROKI TAKAHATA、AKIRA TOMIGUCHI、ATSUSHI HAGIWARA、TAKAO YAMAZAKI

  DOI：10.1248/cpb.30.3959

  日期：——

  Reaction of ketene-S, N-acetals (1a-c) derived from lactams with dimethyl acetylenedicarboxylate (DMAD) gave the ring-expanded products (3a-c, respectively). On the other hand, similar treatment of N-acetyl ketene-S, N-acetals (5b, c) afforded the [2+2] adducts (6b, c, respectively). Next, the reaction of benzoketene-S, N-acetals (8a-c) with DMAD furnished the ringopened products (13a-c, respectively).

  来自内酰胺的酮烯-S,N-乙缩醛（1a-c）与二甲基乙炔二羧酸酯（DMAD）反应，得到了环扩张产物（3a-c，分别对应）。另一方面，N-乙酰基酮烯-S,N-乙缩醛（5b,c）经过类似处理，形成了[2+2]加合物（6b,c，分别对应）。随后，苯并酮烯-S,N-乙缩醛（8a-c）与DMAD反应，生成了开环产物（13a-c，分别对应）。
• Inverse electron demand diels-alder reactions of 5-nitropyrimidine with enamines. synthesis of 3-nitropyridine derivatives
  作者：Antonius T.M. Marcelis、Henk C. Van Der Plas

  DOI：10.1016/s0040-4020(01)80099-5

  日期：1989.1

  The reaction of cyclic and non-cyclic enamines with 5-nitropyrimidine has been studied. Many enamines react in an inverse electron-demand Diels-Alder reaction, leading to the formation of 3-nitropyridines. N,S-ketene acetals were also found to react with 5-nitropyrimidine. The mechanism of the reaction will be discussed.

  已经研究了环状和非环状烯胺与5-硝基嘧啶的反应。许多烯胺以反电子需求的狄尔斯-阿尔德反应进行反应，导致形成3-硝基吡啶。还发现N，S-乙烯酮缩醛与5-硝基嘧啶反应。将讨论该反应的机理。
• Takahata, Hiroki; Tomiguch, Akira; Yamazaki, Takao, Heterocycles, 1981, vol. 16, # 9, p. 1569 - 1572
  作者：Takahata, Hiroki、Tomiguch, Akira、Yamazaki, Takao

  DOI：——

  日期：——
• Marcelis, Antonius T. M.; Plas, Henk C. van der, Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 545 - 548
  作者：Marcelis, Antonius T. M.、Plas, Henk C. van der

  DOI：——

  日期：——
• Takahata, Hiroki; Nakano, Masaharu; Tomiguhi, Akira, Heterocycles, 1982, vol. 17, p. 413 - 416
  作者：Takahata, Hiroki、Nakano, Masaharu、Tomiguhi, Akira、Yamazaki, Takao

  DOI：——

  日期：——