ethyl 3-methylthio-1,2,4-triazin-5-yl ketone | 153462-02-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 3-methylthio-1,2,4-triazin-5-yl ketone
• 英文别名: 3-methylsulfanyl-5-propanoyl-1,2,4-triazine；5-propanoyl-3-methylsulfanyl-1,2,4-triazine；3-(methylthio)-5-propanoyl-1,2,4-triazine；1-(3-methylsulfanyl-1,2,4-triazin-5-yl)propan-1-one
• CAS: 153462-02-3
• 化学式: C₇H₉N₃OS
• 分子量: 183.234
• InChiKey: GVYQXQPPBLAGMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  360.2±34.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-methylthio-1,2,4-triazin-5-yl ketone 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.08h， 生成 5-ethyl-3-(methylthio)-7-(p-chlorophenyl)pyrazolo[4,3-e][1,2,4]triazine
  参考文献：
  名称：

  摘要：

  The reaction of 3-(methylthio)-5-propanoyl-1,2,4-triazine with p-chlorophenylhydrazine hydrochloride is completed within 5 min at room temperature in ethanol leading to p-chlorophenylhydrazone of 3-(methylthio)-5-propanoyl-1,2,4-triazine 1 in good yield. Title compound, 1 (R = C2H5, R-1 = Cl, Z = SCH3), C13H14N5SCl, crystallizes in the monoclinic system, space group P2(1)/n, with cell constants a = 12.5206(6) Angstrom, b = 9.3122(8) Angstrom, c = 12.8524(9) Angstrom, and beta = 98.822(5)degrees, Z = 4, T = 293 K, D-cal = 1.381 g cm(-3). The structure was solved by direct methods and refined to R value of 0.0671 for 1,679 reflections. The molecule as a whole has an almost planar conformation and possesses (E) configuration with respect to the C=N double bond. The crystal structure is stabilized by a weak N(13)-H(13). . .N(2) intermolecular hydrogen bond and significant stacking, characteristic for pi -electron systems.

  DOI：

  10.1023/a:1009590124194
• 作为产物：
  描述：

  N-[1-(3-methylsulfanyl-1,2,4-triazin-5-yl)propylidene]hydroxylamine 在 ammonium chlorochromate on aluminum oxide 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以90%的产率得到ethyl 3-methylthio-1,2,4-triazin-5-yl ketone
  参考文献：
  名称：

  通过 5-ACYL-1,2,4-TRIAZLNES 的反电子需求狄尔斯-阿尔德反应合成 2-酰基吡啶的新方法

  摘要：

  具有合适的氮杂二烯排列的杂芳族系统的逆电子需求 Diels-Alder 反应目前在合成杂环方面具有重要的实际用途。1,2,4Triazines 可以以多种方式作为 Diels-Alder 氮杂二烯与富含电子的亲二烯体反应生成加成产物，随后在逆 Diels-Alder 反应步骤中生成其他杂环系统。这种反应提供了获得新型吡啶或嘧啶的途径，并且已被用于天然产物、生物活性化合物 3 或配位化学配体的全合成......在我们对两性离子吲哚生物碱感兴趣的背景下，我们需要3-乙酰基-5,6,7,8-四氢异喹啉 (2) (R = H) 的方便合成，用于制备 sempervirine。该化合物以前是从环己酮 (1) 开始的八步合成中获得的；然而，2 的整体产量非常低。使用 Diels-Alder 环化方法，我们能够以 8 1 % 的产率从 5-酰基-3 甲基硫烷基 I,2,4-三嗪 5e 和 1-吡咯烷基环己烯制备

  DOI：

  10.1080/00304940109356617

文献信息

• Transformations of phenylhydrazones of 5-acyl-1,2,4-triazines to pyrazolo[4,3-<i>e</i>][1,2,4]triazines or 4-cyanopyrazole
  作者：Mariusz Mojzych、Andrzej Rykowski

  DOI：10.1002/jhet.5570440504

  日期：2007.9

  A simple and high yielding preparation of pyrazolo[4,3-e][1,2,4]triazines and 4-cyano-3-methyl-1-phenylpyrazole derivatives from corresponding phenylhydrazones of 5-acyl-1,2,4-triazines by melt under acidic medium and by thermal heating, respectively.

  由5-酰基-1,2,4-的相应苯hydr类化合物简单高效地制备吡唑并[4,3- e ] [1,2,4]三嗪和4-氰基-3-甲基-1-苯基吡唑衍生物通过在酸性介质下熔融和通过热加热分别形成三嗪。
• Palladium-catalyzed cross-coupling of 5-acyl and 5-formyl-1,2,4-triazines and their derivatives with heteroaromatic tin compounds
  作者：Danuta Branowska、Ewa Olender、Andrzej Rykowski

  DOI：10.1016/j.tet.2014.04.094

  日期：2014.8

  mono- and di(substituted)-1,2,4-triazine derivatives containing thiophene and furan rings are described. Heteroaromatic rings were provided using palladium-catalyzed cross-coupling reaction between 3-alkylsulfanyl-5-acyl-1,2,4-triazines or 5-cyano-3-alkylsulfanyl-1,2,4-triazines and heteroaromatic tin compounds. New compounds bearing masked acyl groups were also obtained. These reactions were optimized

  描述了含有噻吩和呋喃环的新型单和二（取代）-1,2,4-三嗪衍生物的合成。使用3-烷基硫烷基-5-酰基-1，2，4-三嗪或5-氰基-3-烷基硫烷基-1，2，4-三嗪与杂芳族锡化合物之间的钯催化交叉偶联反应提供杂芳族环。还获得了带有掩蔽酰基的新化合物。这些反应经过优化以确定该方法的范围和局限性，并用于制备带有末端杂环的寡聚噻吩。
• A New Synthesis of Pyrazolo- [4,3-e][1,2,4]triazines via Acid Promoted Ring Closure of the Phenylhydrazones of 5-Acyl-1,2,4-triazines
  作者：Andrzej Rykowski、Mariusz Mojzych、Zbigniew Karczmarzyk

  DOI：10.3987/com-00-8972

  日期：——

  The reaction of various substituted phenylhydrazones of 5-acyl-1,2,4-triazines in the presence of 1.1 equivalent of HCl in boiling ethanol-dioxane mixture has been studied. In all reactions the formation of the corresponding pyrazolo[4,3-e][1,2,4]triazines (3a-r) takes place in good yield. The structures of 3a-r were unequivocally established by spectroscopic methods as well as by X-Ray analysis of selected 5-methyl-3-phenyl-7-(p-tolyl)pyrazolo[4,3-e] [1,2,4]triazine (3a).
• An unusual transformation of 5-acyl-1,2,4-triazines into 3-pyridyl-1,2,4-triazines via tandem Stille cross-coupling/aza Diels–Alder reaction
  作者：Danuta Branowska、Olga Siuchta、Zbigniew Karczmarzyk、Waldemar Wysocki、Ewa Wolińska、Mariusz Mojzych、Robert Kawęcki

  DOI：10.1016/j.tetlet.2011.10.034

  日期：2011.12

  A new route to 3-heteroaryl-1,2,4-triazines possessing a keto substituent at C-5 of the 1,2,4-triazine core using a Stille cross-coupling procedure and their unexpected ring transformation into pyridyltriazines as a result of enolization of an acyl group catalyzed by metal ions, are reported. (C) 2011 Elsevier Ltd. All rights reserved.
• Mojzych, Mariusz; Sebela, Marek, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 2, p. 300 - 305
  作者：Mojzych, Mariusz、Sebela, Marek

  DOI：——

  日期：——