3,5-dichloro-1,6-diphenyl-2(1H)-pyrazinone | 138610-69-2

• 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: 3,5-dichloro-1,6-diphenyl-2(1H)-pyrazinone
• 英文别名: 3,5-Dichloro-1,6-diphenylpyrazin-2-one
• CAS: 138610-69-2
• 化学式: C₁₆H₁₀Cl₂N₂O
• 分子量: 317.174
• InChiKey: UHTHHLMTRLWHSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dichloro-1,6-diphenyl-2(1H)-pyrazinone 在 四(三苯基膦)钯 potassium carbonate 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以52%的产率得到6,6'-Dichloro-4,5,4',5'-tetraphenyl-4H,4'H-[2,2']bipyrazinyl-3,3'-dione
  参考文献：
  名称：

  Synthesis of Novel Functionalised Symmetric Bi-2(1H)-pyrazinones

  摘要：

  本文介绍了一种简单方便的合成方法，即从 3,5-二氯-2(1H)-吡嗪酮 7、10a-h 开始，合成功能化双-2(1H)-吡嗪酮 9、11a-h。吡嗪酮是通过原位生成的硼酸盐的苏木型反应进行均偶合的。反应在常规加热和微波辐照条件下进行，在微波辐照条件下，反应的速率和产率都有显著提高。

  DOI：

  10.1055/s-2005-863747

文献信息

• A Chemoselective Microwave-Assisted One-Pot Cross-Stille Reaction of Benzylic Halides with 2(1<i>H</i>)-Pyrazinones Using Simultaneous Cooling
  作者：Erik Van der Eycken、Prasad Appukkuttan、Mofazzal Husain、Rajinder Gupta、Virinder Parmar

  DOI：10.1055/s-2006-941607

  日期：2006.6

  This manuscript reports the chemoselective one-pot cross-Stille coupling of benzylic halides with 3,5-dichloro-2(1H)-pyrazinones, which avoids the purification and handling of toxic stannylated intermediates. Significant improvements in yields were established when microwave irradiation was performed with simultaneous cooling.

  本手稿报告了苄基卤化物与 3,5-二氯-2(1H)-吡嗪酮的化学选择性一锅交叉-斯蒂尔偶联反应，该反应避免了纯化和处理有毒的星烷化中间体。在进行微波辐照的同时进行冷却，可显著提高产量。
• Cycloadducts of ethene with 2(1H)-pyrazinones and their conversion into 2,5-diazabicyclo[2.2.2]octane-3,6-diones.
  作者：Patrick K. Loosen、Mayoka G. Tutonda、Masoumeh F. Khorasani、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96214-3

  日期：1991.11

  Cycloaddition of variously substituted 2(1H)-pyrazinones with ethene and subsequent hydrolysis of the adducts 2 provides a general and efficient route to the title compounds 3. Compound 3m was used as a building block for a structural analogue of gliotoxin.
• Synthesis of pyrazino[1,2-a]benzimidazol-1(2H)ones via a microwave assisted Buchwald–Hartwig type reaction
  作者：Jo Alen、Koen Robeyns、Wim M. De Borggraeve、Luc Van Meervelt、Frans Compernolle

  DOI：10.1016/j.tet.2008.06.056

  日期：2008.8

  A convenient synthesis of substituted pyrazino[1,2-a]benzimidazol-1(2H)ones starting from 3,5-dichloropyrazinones has been accomplished. Various 3-anilino-pyrazinones were easily converted to the desired tricyclic structures by applying a microwave assisted Buchwald-Hartwig type cyclization. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 2(1<i>H</i>)-Pyrazinone Phosphonates via an Arbuzov-type Reaction
  作者：Jo Alen、Liliana Dobrzańska、Wim M. De Borggraeve、Frans Compernolle

  DOI：10.1021/jo062176a

  日期：2007.2.1

  A simple and catalyst-free method for the synthesis of phosphonated 2(1H)-pyrazinones is described starting from 3,5-dichloropyrazinones. The method also works for 3-bromo- and 3-iodopyrazinones. Classical heating conditions as well as microwave-enhanced reaction conditions were tested.
• US5364869A
  申请人：——

  公开号：US5364869A

  公开（公告）日：1994-11-15