5-phenyl-3-vinyl-1,2,4-triazine | 1222866-97-8

• 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: 5-phenyl-3-vinyl-1,2,4-triazine
• 英文别名: 3-Ethenyl-5-phenyl-1,2,4-triazine；3-ethenyl-5-phenyl-1,2,4-triazine
• CAS: 1222866-97-8
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: SFTLFECBCYOJCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  387.5±35.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenyl-3-vinyl-1,2,4-triazine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯苯 、 乙腈 为溶剂， 反应 21.0h， 生成 4-methyl-2-phenyl-7,8-dihydro-5H-thiopyrano[4,3-b]pyridine
  参考文献：
  名称：

  有机催化的Thia-Michael加成反应和对3-乙烯基-1,2,4-三嗪平台的顺序电子逆序Diels-Alder反应

  摘要：

  这项工作强调了将3-乙烯基-1,2,4-三嗪用作原始的thia-Michael受体和要求反电子的Diels-Alder平台，用于新的7,8-dihydro-5 H -thiopyrano [4,3- b ]吡啶。所需但相当不稳定的炔丙基硫醇亲核试剂是在相应的炔丙基硫代乙酸酯衍生物的创新性DBU催化甲醇分解事件中成功地原位生成的。

  DOI：

  10.1002/adsc.201700831
• 作为产物：
  描述：

  乙烯基溴化镁 、 3-(methylsulfonyl)-5-phenyl-1,2,4-triazine 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到5-phenyl-3-vinyl-1,2,4-triazine
  参考文献：
  名称：

  SAR studies on new bis-aryls 5-HT7 ligands: Synthesis and molecular modeling

  摘要：

  Structure-activity relationships of a series of bis-arylic compounds, investigated as 5-HT7R ligands, are reported. The main structural modifications involved a central aryl moiety (phenyl, pyridine, diazine, triazine) and the nature and position of an amine-containing aliphatic chain. The affinity of the synthesized compounds (26 nM-10 mu M) was systematically correlated with other previously reported series of bis-arylic ligands and rationalized by a ligand-based pharmacophore approach. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.035

文献信息

• Sequential Michael Addition and Enamine-Promoted Inverse Electron Demanding Diels–Alder Reaction upon 3-Vinyl-1,2,4-triazine Platforms
  作者：Magali Lorion、Gérald Guillaumet、Jean-François Brière、Franck Suzenet

  DOI：10.1021/acs.orglett.5b01487

  日期：2015.6.19

  An original one-pot Michael addition-ihDA/rDA sequence was achieved from 3-vinyl-1,2,4-triazine platforms used as unprecedented Michael acceptors. This sequence provides a novel access to functionalized [2,3]-fused pyridine derivatives via a unique enamine promoted intramolecular ihDA reaction of 1,2,4-triazine intermediates.

  最初的一锅迈克尔加成反应-ih DA / r DA序列是从用作前所未见的迈克尔受体的3-乙烯基-1,2,4-三嗪平台获得的。此序列提供通过独特的烯胺的新颖存取官能[2,3] -融合吡啶衍生物促进分子内IH的1,2,4-三嗪中间体DA反应。
• Organocatalytic aza-Michael Reaction to 3-Vinyl-1,2,4-triazines as a Valuable Bifunctional Platform
  作者：Floris Buttard、Clément Berthonneau、Marie-Aude Hiebel、Jean-François Brière、Franck Suzenet

  DOI：10.1021/acs.joc.9b00141

  日期：2019.3.15

  original bifunctional platforms for the domino conjugate addition inverse-electron-demand hetero-Diels–Alder/retro-Diels–Alder (ihDA/rDA) reaction, was achieved using the highly acidic triflimide as an organocatalyst. Based on the use of alkoxyamine nucleophiles, this sequence not only highlights a rare example of the catalytic aza-Michael reaction to alkenylazaarenes but also proves to be useful for the elaboration

  空前的催化氮杂-迈克尔加成反应，取代了3-乙烯基-1,2,4-三嗪，作为多米诺共轭物加成反应的反向双电子平台，反电子需求异Diels–Alder / RetroDiels–Alder（ih DA /使用高度酸性的三氟甲酰亚胺作为有机催化剂可实现r DA）反应。基于烷氧基胺亲核试剂的使用，该序列不仅突出了催化氮杂-迈克尔与链烯基氮杂芳烃反应的罕见实例，而且还证明可用于制备一系列与生物有关的四氢-[1,6]-萘啶。
• Domino Aza-Michael-<i>ih</i>-Diels–Alder Reaction to Various 3-Vinyl-1,2,4-triazines: Access to Polysubstituted Tetrahydro-1,6-naphthyridines
  作者：Jabrane Jouha、Floris Buttard、Magali Lorion、Clément Berthonneau、Mostafa Khouili、Marie-Aude Hiebel、Gérald Guillaumet、Jean-François Brière、Franck Suzenet

  DOI：10.1021/acs.orglett.7b02132

  日期：2017.9.15

  A straightforward domino aza-Michael-inverseelectron-demand-hetero-Diels Alder/retro-Diels-Alder reaction between primary and secondary propargylamine derivatives and 3-vinyl-1,2,4-triazines is developed highlighting not only the uniqueness of this dual-heterocyclic platform but also a novel and unprecedented path to polysubstituted tetrahydro-1,6-naphthyridine scaffolds.
• SAR studies on new bis-aryls 5-HT7 ligands: Synthesis and molecular modeling
  作者：Eduard Badarau、Ryszard Bugno、Franck Suzenet、Andrzej J. Bojarski、Adriana-Luminita Finaru、Gérald Guillaumet

  DOI：10.1016/j.bmc.2010.01.035

  日期：2010.3

  Structure-activity relationships of a series of bis-arylic compounds, investigated as 5-HT7R ligands, are reported. The main structural modifications involved a central aryl moiety (phenyl, pyridine, diazine, triazine) and the nature and position of an amine-containing aliphatic chain. The affinity of the synthesized compounds (26 nM-10 mu M) was systematically correlated with other previously reported series of bis-arylic ligands and rationalized by a ligand-based pharmacophore approach. (C) 2010 Elsevier Ltd. All rights reserved.
• Organocatalyzed Thia-Michael Addition and Sequential Inverse Electron Demanding Diels-Alder Reaction to 3-Vinyl-1,2,4- triazine Platforms
  作者：Clément Berthonneau、Floris Buttard、Marie-Aude Hiebel、Franck Suzenet、Jean-François Brière

  DOI：10.1002/adsc.201700831

  日期：2017.12.11

  This work highlights the use of 3-vinyl-1,2,4-triazines as original thia-Michael acceptors and inverse electron demanding Diels-Alder platforms en route to new 7,8-dihydro-5H-thiopyrano[4,3-b]pyridines. The required but rather unstable propargylthiol nucleophiles were successfully generated in-situ upon an innovative DBU-catalyzed methanolysis event of the corresponding propargyl thioacetate derivatives

  这项工作强调了将3-乙烯基-1,2,4-三嗪用作原始的thia-Michael受体和要求反电子的Diels-Alder平台，用于新的7,8-dihydro-5 H -thiopyrano [4,3- b ]吡啶。所需但相当不稳定的炔丙基硫醇亲核试剂是在相应的炔丙基硫代乙酸酯衍生物的创新性DBU催化甲醇分解事件中成功地原位生成的。