2-chloro-3-vinylpyrazine | 1512811-30-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-chloro-3-vinylpyrazine
• 英文别名: 2-Chloro-3-ethenylpyrazine；2-chloro-3-ethenylpyrazine
• CAS: 1512811-30-1
• 化学式: C₆H₅ClN₂
• 分子量: 140.572
• InChiKey: DNHCWLZLWADATO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-vinylpyrazine 、 2-氨基苯硼酸频哪醇酯 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯(2-二环己基膦基-2',6'-二异丙氧基-1,1'-联苯)[2-(2-氨基乙基苯基)]钯(II) 、 potassium hydroxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以90%的产率得到10,11-dihydro-5H-benzo[b]pyrazino[2,3-f]azepine
  参考文献：
  名称：

  Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process

  摘要：

  In recent years, our group has been developing Multicatalytic reactions for the synthesis of biologically relevant heterocyclic compounds. An efficient dual-metal catalyzed reaction of electron-deficient o-chlorovinylpyridines with o-aminophenylboronic esters to access pyridobenzazepines is described. Combining a Rh-I-catalyzed arylation followed by a Pd-catalyzed C-N coupling, in a one-pot procedure, provides a simplified method to access heterocycles without workup and purification after each step. The substrate scope encompasses a variety of N-H and N-alkylated pyridobenzazepine variants with yields up to 93%.

  DOI：

  10.1021/acs.joc.7b00568
• 作为产物：
  描述：

  2-氯-3-碘吡嗪 、 乙烯三氟硼酸钾 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以55%的产率得到2-chloro-3-vinylpyrazine
  参考文献：
  名称：

  Multicomponent-Multicatalyst Reactions (MC)²R: Efficient Dibenzazepine Synthesis

  摘要：

  A Rh-I/Pd-0 catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.

  DOI：

  10.1021/ol4030925

文献信息

• Multicomponent-Multicatalyst Reactions (MC)²R: Efficient Dibenzazepine Synthesis
  作者：Jennifer Tsoung、Jane Panteleev、Matthias Tesch、Mark Lautens

  DOI：10.1021/ol4030925

  日期：2014.1.3

  A Rh-I/Pd-0 catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.
• Synthesis of Pyridobenzazepines Using a One-Pot Rh/Pd-Catalyzed Process
  作者：Heather Lam、Jennifer Tsoung、Mark Lautens

  DOI：10.1021/acs.joc.7b00568

  日期：2017.6.16

  In recent years, our group has been developing Multicatalytic reactions for the synthesis of biologically relevant heterocyclic compounds. An efficient dual-metal catalyzed reaction of electron-deficient o-chlorovinylpyridines with o-aminophenylboronic esters to access pyridobenzazepines is described. Combining a Rh-I-catalyzed arylation followed by a Pd-catalyzed C-N coupling, in a one-pot procedure, provides a simplified method to access heterocycles without workup and purification after each step. The substrate scope encompasses a variety of N-H and N-alkylated pyridobenzazepine variants with yields up to 93%.