5-chloro-3-(diethylamino)-1-phenyl-2(1H)-pyrazinone | 139706-32-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-chloro-3-(diethylamino)-1-phenyl-2(1H)-pyrazinone
• 英文别名: 2(1H)-Pyrazinone, 5-chloro-3-(diethylamino)-1-phenyl-；5-chloro-3-(diethylamino)-1-phenylpyrazin-2-one
• CAS: 139706-32-4
• 化学式: C₁₄H₁₆ClN₃O
• 分子量: 277.754
• InChiKey: SUUUXPIJNMVZJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.4±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-3-(diethylamino)-1-phenyl-2(1H)-pyrazinone 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到3-(diethylamino)-1-phenyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Cycloaddition of 3-Amino-5-chloro-2(1H)-pyrazinones and Olefins:  Ring Transformation into 3-Amino- or 6-Cyano-Substituted 2-Pyridinone Systems

  摘要：

  The cycloadducts formed from the Diels-Alder reaction of 3-amino-5-chloro-2(1H)-pyrazinones with methyl acrylate in toluene are subject to two alternative modes of ring transformation yielding either methyl 6-cyano-1,2-dihydro-2-oxo-4-pyridinecarboxylates, e.g. 12a,b (loss of amine substituent), or the corresponding 3-amino-6-cyano-1,2,5,6-tetrahydro-2-oxo-4-pyridecarboxylates, e.g. 15a,b. From the latter compounds, 3-amino-2-pyridinones can be generated through subsequent loss of HCN. A mechanism accounting for the loss or retention of the amine substituent is based on (1) the effects observed for each reaction mode when varying the substituents in both reaction partners and (2) the exclusive retention of the amine substituent when replacing toluene with the basic solvent pyridine.

  DOI：

  10.1021/jo951016o
• 作为产物：
  描述：

  3,5-二氯-1-苯基吡嗪-2(1H)-酮 、 二乙胺 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以94%的产率得到5-chloro-3-(diethylamino)-1-phenyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Ring transformations of 3-(diethylamino)-5-chloro-2(1H)-pyrazinones and the corresponding 2H-1,4-oxazin-2-ones on reaction with acetylenic compounds

  摘要：

  DOI：

  10.1021/jo00036a033

文献信息

• Ring transformations of 3-(diethylamino)-5-chloro-2(1H)-pyrazinones and the corresponding 2H-1,4-oxazin-2-ones on reaction with acetylenic compounds
  作者：Mayoka G. Tutonda、Stef M. Vandenberghe、Koen J. Van Aken、Georges J. Hoornaert

  DOI：10.1021/jo00036a033

  日期：1992.5
• Cycloaddition of 3-Amino-5-chloro-2(1<i>H</i>)-pyrazinones and Olefins:  Ring Transformation into 3-Amino- or 6-Cyano-Substituted 2-Pyridinone Systems
  作者：Stef M. Vandenberghe、Kris J. Buysens、Lieven Meerpoel、Patrick K. Loosen、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1021/jo951016o

  日期：1996.1.1

  The cycloadducts formed from the Diels-Alder reaction of 3-amino-5-chloro-2(1H)-pyrazinones with methyl acrylate in toluene are subject to two alternative modes of ring transformation yielding either methyl 6-cyano-1,2-dihydro-2-oxo-4-pyridinecarboxylates, e.g. 12a,b (loss of amine substituent), or the corresponding 3-amino-6-cyano-1,2,5,6-tetrahydro-2-oxo-4-pyridecarboxylates, e.g. 15a,b. From the latter compounds, 3-amino-2-pyridinones can be generated through subsequent loss of HCN. A mechanism accounting for the loss or retention of the amine substituent is based on (1) the effects observed for each reaction mode when varying the substituents in both reaction partners and (2) the exclusive retention of the amine substituent when replacing toluene with the basic solvent pyridine.