(4-chlorophenyl)(3-chloropyrazin-2-yl)methanone | 1392271-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-chlorophenyl)(3-chloropyrazin-2-yl)methanone
• 英文别名: (4-Chlorophenyl)-(3-chloropyrazin-2-yl)methanone
• CAS: 1392271-92-9
• 化学式: C₁₁H₆Cl₂N₂O
• 分子量: 253.087
• InChiKey: BWRFRPFMNGYMIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)(3-chloropyrazin-2-yl)methanone 在 吡啶 、 氨 、 palladium diacetate 、 tetra-N-butylammonium tribromide 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 水 、 乙二醇 、 甲苯 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-amino-3-(4-chlorobenzyl)-5-phenylpyrazine
  参考文献：
  名称：

  New red-shifted coelenterazine analogues with an extended electronic conjugation

  摘要：

  A new promising approach to the development of red-shifted coelenterazine analogues was described. In order to alter the photochemical properties of native coelenterazine, we have designed and synthesized analogues bearing a new electron-rich structure. The spectroscopic results obtained, in the presence of the target enzyme (Renilla Luciferase), show a bathochromic emission shift of the entire class of new derivatives. Among them, the 2-benzyl-8-(4-chlorophenylthio)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (8) shows an emission at 510 nm and uncommon slow kinetic decay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.041
• 作为产物：
  描述：

  2-氯吡嗪 、 4-氯苯甲酰氯 在 zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以40%的产率得到(4-chlorophenyl)(3-chloropyrazin-2-yl)methanone
  参考文献：
  名称：

  New red-shifted coelenterazine analogues with an extended electronic conjugation

  摘要：

  A new promising approach to the development of red-shifted coelenterazine analogues was described. In order to alter the photochemical properties of native coelenterazine, we have designed and synthesized analogues bearing a new electron-rich structure. The spectroscopic results obtained, in the presence of the target enzyme (Renilla Luciferase), show a bathochromic emission shift of the entire class of new derivatives. Among them, the 2-benzyl-8-(4-chlorophenylthio)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (8) shows an emission at 510 nm and uncommon slow kinetic decay. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.041

文献信息

• A Convenient Two-Step Synthesis of 7-Aryl-6,7-dihydrothieno[2,3-b]pyrazines from Aryl(3-chloropyrazin-2-yl)methanones
  作者：Kazuhiro Kobayashi、Teruhiko Suzuki

  DOI：10.3987/com-13-12728

  日期：——

  An efficient method for the preparation of 7-aryl-6,7-dihydrothieno[2,3-b]pyrazines (3) under mild conditions has been developed. The reaction of aryl(3-chloropyrazin-2-yl)methanones (1), derived from commercially available 2-chloropyrazine, with methylenetriphenylphosphorane in THF at room temperature gave the corresponding 2-(1-arylethenyl)-3-chloropyrazines (2), which were treated with NaSH center dot nH(2)O in DMF at room temperature to lead to the desired products (3) in acceptable yields. These products are dehydrogenated with air in refluxing toluene in the presence of a catalytic amount of Pd/C to yield the corresponding 7-arylthieno [2,3-b]pyrazines (4).