3-[(E)-2-phenylethenyl]-1,2,4-triazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[(E)-2-phenylethenyl]-1,2,4-triazine
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: YJVOFSNVARPYJC-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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

• 作为产物：
  描述：

  在 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以24 mg的产率得到3-[(E)-2-phenylethenyl]-1,2,4-triazine
  参考文献：
  名称：

  1,2,4-Triazines Are Versatile Bioorthogonal Reagents

  摘要：

  A new class of bioorthogonal reagents, 1,2,4-triazines, is described. These scaffolds are Stable in biological media and capable of robust reactivity with trans-cyclooctene (TCO). The enhanced stability of the triazine scaffold enabled its direct use in recombinant protein production. The triazine-TCO reaction can also be used in tandem with other bioorthogonal cycloaddition reactions. These features fill current voids in the bioorthogonal toolkit.

  DOI：

  10.1021/jacs.5b05100

文献信息

• Palladium-catalyzed 3-Thiomethyltriazine-boronic Acid Cross Coupling: Easy Access to 3-Substituted-1,2,4-triazines
  作者：France-Aimée Alphonse、Franck Suzenet、Anne Keromnes、Bruno Lebret、Gérald Guillaumet

  DOI：10.1055/s-2002-20462

  日期：——

  The palladium-catalyzed coupling reaction of 3-thiomethyl-1,2,4-triazine 1 with different organoboron compounds in the presence of copper(I) 3-methylsalicylate proceeds to afford the corresponding 3-substituted-1,2,4-triazines in good yield. This approach leads very easily to a large range of C-5 and C-6 unsubstituted as-triazines.

  在铜(I) 3-甲基水杨酸盐的存在下，钯催化的3-硫甲基-1,2,4-三嗪1与不同的有机硼化合物的偶联反应顺利进行，获得相应的3-取代-1,2,4-三嗪，产率良好。这种方法非常容易得到多种C-5和C-6未取代的三嗪类化合物。
• A General Approach to Selective Functionalization of 1,2,4-Triazines Using Organometallics in Palladium-Catalyzed Cross-Coupling and Addition Reactions
  作者：Gérald Guillaumet、France-Aimée Alphonse、Franck Suzenet、Anne Keromnes、Bruno Lebret

  DOI：10.1055/s-2004-834868

  日期：——

  A selective way to obtain disubstituted 1,2,4-triazines in good yields by combining addition reactions and palladium-catalyzed cross-coupling reactions of organometallics with 3-methylsulfanyl-1,2,4-triazine is described.

  描述了一种通过结合有机金属与 3-甲基硫烷基-1,2,4-三嗪的加成反应和钯催化的交叉偶联反应以高收率获得二取代 1,2,4-三嗪的选择性方法。
• Copper(I)-Promoted Palladium-Catalyzed Cross-Coupling of Unsaturated Tri-<i>n</i>-butylstannane with Heteroaromatic Thioether
  作者：France-Aimée Alphonse、Franck Suzenet、Anne Keromnes、Bruno Lebret、Gérald Guillaumet

  DOI：10.1021/ol027453o

  日期：2003.3.1

  [reaction: see text] Palladium-catalyzed cross-coupling of vinyl- and arylstannanes with pi-electron-deficient heteroaromatics was performed in good yields. This Stille-type reaction was carried out with a methylthioether function as an electrophile in the presence of a copper(I) bromide-dimethyl sulfide complex.

  [反应：见正文]钯催化的乙烯基和芳基锡烷与π电子缺陷型杂芳族化合物的交叉偶联反应收率很高。该Stille型反应是在溴化铜（I）-二甲基硫醚络合物的存在下，以甲硫醚作为亲电试剂进行的。
• 1,2,4-Triazines Are Versatile Bioorthogonal Reagents
  作者：David N. Kamber、Yong Liang、Robert J. Blizzard、Fang Liu、Ryan A. Mehl、K. N. Houk、Jennifer A. Prescher

  DOI：10.1021/jacs.5b05100

  日期：2015.7.8

  A new class of bioorthogonal reagents, 1,2,4-triazines, is described. These scaffolds are Stable in biological media and capable of robust reactivity with trans-cyclooctene (TCO). The enhanced stability of the triazine scaffold enabled its direct use in recombinant protein production. The triazine-TCO reaction can also be used in tandem with other bioorthogonal cycloaddition reactions. These features fill current voids in the bioorthogonal toolkit.