1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine | 287102-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine
• CAS: 287102-93-6
• 化学式: C₁₅H₁₈N₄O₄S₂
• 分子量: 382.464
• InChiKey: PYIKQSLGCLAAOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine 在 溴苯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 生成 7-(1-methylsulfonyl-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridin-3-yl)-3,4-dihydro-2H-pyrano[2,3-b]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：

  1-Methylsulfanyl-3-(3-methylsulfanyl-[1,2,4]triazin-5-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine 在 四丁基溴化铵 potassium permanganate 作用下， 以 溶剂黄146 、 苯 为溶剂， 以93%的产率得到1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine
  参考文献：
  名称：

  一种新的一锅合成的稠2,2'-联吡啶配体由5,5-逆电子需求Diels-Alder反应' -bi -1,2,4-三嗪1

  摘要：

  5,5'-联-1,2,4-三嗪与环状烯胺的狄尔斯-阿尔德反应在不存在溶剂的情况下可产生一系列对称的，环状的2,2'-联吡啶，并具有良好的收率。当反应在沸腾的二恶烷中进行时，仅形成5-（杂芳基）1,2,4-三嗪。后者带有甲基硫烷基取代基，被高锰酸钾氧化成相应的甲基磺酰基衍生物，很容易与不同的烯胺进行Diels-Alder反应，生成不对称的环状2,2'-联吡啶。

  DOI：

  10.1016/s0040-4039(00)00436-6

文献信息

• A Convenient Method of Preparation of 3,3’-Dichloro-5,5’-bi-1,2,4-triazine and Its Synthetic Applications
  作者：Ewa Wolińska

  DOI：10.3987/com-08-11535

  日期：——

  A convenient method for preparing of 3,3'-dichloro-5,5'-l,2,4-triazine (4) and its application to the synthesis of 3,3'-diamino-5,5'-bi-l,2,4-triazines 6a-i by the nucleophilic aromatic substitution are described. An attempt to synthesis of cyclophanes containing 5,5'-bi-l,2,4-triazine subunit by ring-closing metathesis of the alkenyl ethers 7a,b have been unsuccessful. A crossover experiment clearly

  3,3'-二氯-5,5'-l,2,4-三嗪(4)的简便制备方法及其在3,3'-二氨基-5,5'-bi-l合成中的应用描述了通过亲核芳族取代的 ,2,4-三嗪 6a-i。通过烯基醚 7a、b 的闭环复分解来合成含有 5,5'-双-1,2,4-三嗪亚基的环烷的尝试没有成功。交叉实验清楚地表明，1,2,4-三嗪环的氮原子与钌催化剂配位并使其失活。
• 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.
• A novel one-pot synthesis of annulated 2,2′-bipyridine ligands by inverse electron demand Diels–Alder reaction of 5,5′-bi-1,2,4-triazines
  作者：Andrzej Rykowski、Danuta Branowska、Joanna Kielak

  DOI：10.1016/s0040-4039(00)00436-6

  日期：2000.5

  The Diels–Alder reaction of 5,5′-bi-1,2,4-triazines with cyclic enamines in the absence of a solvent leads to a range of symmetrical, annulated 2,2′-bipyridines in good yield. When the reaction is carried out in boiling dioxane only 5-(heteroaryl)1,2,4-triazines are formed. The latter, bearing methylsulfanyl substituents, are oxidized with potassium permanganate to the corresponding methylsulfonyl

  5,5'-联-1,2,4-三嗪与环状烯胺的狄尔斯-阿尔德反应在不存在溶剂的情况下可产生一系列对称的，环状的2,2'-联吡啶，并具有良好的收率。当反应在沸腾的二恶烷中进行时，仅形成5-（杂芳基）1,2,4-三嗪。后者带有甲基硫烷基取代基，被高锰酸钾氧化成相应的甲基磺酰基衍生物，很容易与不同的烯胺进行Diels-Alder反应，生成不对称的环状2,2'-联吡啶。