1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-5,6,7,8-tetrahydroisoquinoline | 287102-92-5

• 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)-5,6,7,8-tetrahydroisoquinoline
• 英文别名: 1-Methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-5,6,7,8-tetrahydroisoquinoline
• CAS: 287102-92-5
• 化学式: C₁₄H₁₆N₄O₄S₂
• 分子量: 368.437
• InChiKey: NNWLMXPWXSPIDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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)-5,6,7,8-tetrahydroisoquinoline 在 溴苯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-(2,3-dihydrofuro[2,3-b]pyridin-6-yl)-1-methylsulfonyl-5,6,7,8-tetrahydroisoquinoline
  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-吡咯烷-1-环己烯 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， 生成 1-methylsulfonyl-3-(3-methylsulfonyl-1,2,4-triazin-5-yl)-5,6,7,8-tetrahydroisoquinoline
  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

文献信息

• 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。
• Synthesis of Unsymmetrical Annulated 2,2’-Bipyridine Analogues with Attached Cycloalkene and Piperidine Rings via Sequential Diels-Alder Reaction of 5,5’-bi-1,2,4-triazines
  作者：D. Branowska

  DOI：10.3390/10010265

  日期：——

  Synthesis of bisfunctionalized unsymmetrical 2,2’-bipyridines 8 or their sulfonyl derivatives 12a,b are described. They were prepared via the Diels-Alder reaction of 1‑methyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (6) with 3,3’-bis(methyl-sulfanyl)-5,5’-bi-1,2,4-triazine (1). The reaction leads to the single cycloaddition product 7 which undergoes Diels-Alder reaction with cyclic enamines 2a

  描述了双官能化不对称 2,2'-联吡啶 8 或其磺酰基衍生物 12a、b 的合成。它们是通过 1-甲基-4-吡咯烷-1-基-1,2,3,6-四氢吡啶 (6) 与 3,3'-双(甲基-硫烷基)-5,5 的 Diels-Alder 反应制备的'-bi-1,2,4-三嗪 (1)。该反应产生单个环加成产物 7，该产物与环烯胺 2a、b 进行狄尔斯-阿尔德反应，得到不对称的 2,2'-联吡啶衍生物 8，由两个不同的杂环单元组成：环烯[c] 吡啶和 2,6 -萘啶。
• 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.