1-Methylsulfanyl-3-(3-methylsulfanyl-[1,2,4]triazin-5-yl)-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridine | 501117-58-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Methylsulfanyl-3-(3-methylsulfanyl-[1,2,4]triazin-5-yl)-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridine
• 英文别名: 1-(Methylsulfanyl)-3-[3-(methylsulfanyl)-1,2,4-triazin-5-yl]-5,6,7,8,9,10-hexahydrocycloocta[c]pyridine；1-methylsulfanyl-3-(3-methylsulfanyl-1,2,4-triazin-5-yl)-5,6,7,8,9,10-hexahydrocycloocta[c]pyridine
• CAS: 501117-58-4
• 化学式: C₁₆H₂₀N₄S₂
• 分子量: 332.494
• InChiKey: OAPYBXAPVKXBKR-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  535.4±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-Methylsulfanyl-3-(3-methylsulfanyl-[1,2,4]triazin-5-yl)-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridine 在 potassium permanganate 、 tetra(n-tert-butyl)ammonium bromide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.0h， 以98%的产率得到1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-5,6,7,8,9,10-hexahydrocycloocta[c]pyridine
  参考文献：
  名称：

  Application of intramolecular cycloaddition/retro cycloaddition reactions for the synthesis of unsymmetrical 2,2′-bipyridine and 2-benzofuropyrazin-2-ylpyridine analogues

  摘要：

  1,2,4-Triazines bearing cycloalkeno[c]pyridine substituents at the 5-position, 2a-d, prepared by an intermolecular Diels-Alder reaction of bi-5,5-triazines with cyclic enamines, were provided with an alkynyloxy or a 2-cyanophenoxy group at the 3-position of the triazinyl unit. A subsequent intramolecular Diels-Alder reaction of the former, followed by loss of N-2 leads to two new classes of 2,2'-bipyridine analogues containing different heterocyclic units, namely cycloalkeno[c]pyridine and 2,3-dihydrofuro- or 2,3-dihydropyrano[2,3-b]pyridine 8a-h; the intramolecular reaction of the 2-cyanophenoxy compound gives benzo[4,5]furo[2,3-b]pyrazine 10a-c. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.011
• 作为产物：
  描述：

  3,3'-bis(methylsulfanyl)-5,5'-bi-1,2,4-triazine 、 1-[(1E)-1-环辛烯-1-基]吡咯烷 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以68%的产率得到1-Methylsulfanyl-3-(3-methylsulfanyl-[1,2,4]triazin-5-yl)-5,6,7,8,9,10-hexahydro-cycloocta[c]pyridine
  参考文献：
  名称：

  通过 5,5'-bi-1,2,4-三嗪的逆电子需求 Diels-Alder 反应生成对称和不对称环烯 [c] 稠合 2,2'-联吡啶配体的简便途径

  摘要：

  描述了一系列 6,6'-双官能化对称环烯基 [c] 稠合 2,2'-联吡啶 4a-h 或不对称环烯基 [c] 稠合 2,2'-联吡啶 6a-g。它们是通过 3,3'-二取代 5,5'-bi-1,2,4-三嗪 2a,b 与环状烯胺 3a-d 的 Diels-Alder 反应制备的。1-乙烯基咪唑 (3e) 与 2a 的区域选择性反应导致 5-(2-吡啶基)-1,2,4-三嗪 9 与环状烯胺 3a-d 发生 Diels-Alder 反应得到不对称的 2,2'-连接有一个环烯烃环的联吡啶 10a-d。

  DOI：

  10.1055/s-2003-41452

文献信息

• Application of 1-Vinylimidazole in Diels-Alder Reaction of 5,5′-bi-1,2,4-Triazines
  作者：Danuta Branowska、Andrzej Rykowski

  DOI：10.1055/s-2002-34880

  日期：——

  5,5'-bi-1,2,4-Triazines undergo inverse electron demand Diels-Alder reaction with 1-vinylimidazole to give single [4+2] cycloaddition products. The reaction of the latter with cyclic enamines leads to unsymmetrical, 2,2'-bipyridines with attached cycloalkene ring.

  5,5'-bi-1,2,4-Triazines 与 1-乙烯基咪唑发生逆电子需求 Diels-Alder 反应，得到单一的 [4+2] 环加成产物。后者与环状烯胺的反应导致不对称的 2,2'-联吡啶与连接的环烯烃环。
• A Facile Route to Symmetrical and Unsymmetrical Cycloalkeno[<i>c</i>]fused 2,2′-Bipyridine Ligands via Inverse Electron Demand Diels-Alder Reaction of 5,5′-bi-1,2,4-Triazines
  作者：Danuta Branowska

  DOI：10.1055/s-2003-41452

  日期：——

  A series of 6,6'-bisfunctionalized symmetrical cycloalkeno[c]fused 2,2'-bipyridines 4a-h or unsymmetrical cycloalkeno[c]fused 2,2'-bipyridines 6a-g is described. They were prepared by the Diels-Alder reaction of 3,3'-disubstituted 5,5'-bi-1,2,4-triazines 2a,b with cyclic enamines 3a-d. The regioselective reaction of 1-vinylimidazole (3e) with 2a leads to 5-(2-pyridyl)-1,2,4-triazine 9 which undergoes

  描述了一系列 6,6'-双官能化对称环烯基 [c] 稠合 2,2'-联吡啶 4a-h 或不对称环烯基 [c] 稠合 2,2'-联吡啶 6a-g。它们是通过 3,3'-二取代 5,5'-bi-1,2,4-三嗪 2a,b 与环状烯胺 3a-d 的 Diels-Alder 反应制备的。1-乙烯基咪唑 (3e) 与 2a 的区域选择性反应导致 5-(2-吡啶基)-1,2,4-三嗪 9 与环状烯胺 3a-d 发生 Diels-Alder 反应得到不对称的 2,2'-连接有一个环烯烃环的联吡啶 10a-d。
• Application of intramolecular cycloaddition/retro cycloaddition reactions for the synthesis of unsymmetrical 2,2′-bipyridine and 2-benzofuropyrazin-2-ylpyridine analogues
  作者：D Branowska

  DOI：10.1016/j.tet.2004.05.011

  日期：2004.7

  1,2,4-Triazines bearing cycloalkeno[c]pyridine substituents at the 5-position, 2a-d, prepared by an intermolecular Diels-Alder reaction of bi-5,5-triazines with cyclic enamines, were provided with an alkynyloxy or a 2-cyanophenoxy group at the 3-position of the triazinyl unit. A subsequent intramolecular Diels-Alder reaction of the former, followed by loss of N-2 leads to two new classes of 2,2'-bipyridine analogues containing different heterocyclic units, namely cycloalkeno[c]pyridine and 2,3-dihydrofuro- or 2,3-dihydropyrano[2,3-b]pyridine 8a-h; the intramolecular reaction of the 2-cyanophenoxy compound gives benzo[4,5]furo[2,3-b]pyrazine 10a-c. (C) 2004 Elsevier Ltd. All rights reserved.