5-chloro-3-(ethylamino)-1-methyl-2(1H)-pyrazinone

• 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: 5-chloro-3-(ethylamino)-1-methyl-2(1H)-pyrazinone
• 英文别名: 5-Chloro-3-(ethylamino)-1-methylpyrazin-2-one
• 化学式: C₇H₁₀ClN₃O
• 分子量: 187.629
• InChiKey: AITXSLPIILBOFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 5-chloro-3-(ethylamino)-1-methyl-2(1H)-pyrazinone 以 甲苯 为溶剂， 反应 120.0h， 以80%的产率得到methyl 6-cyano-3-(ethylamino)-1,2,5,6-tetrahydro-1-methyl-2-oxo-4-pyridinecarboxylate
  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：

  乙胺盐酸盐 、 3,5-二氯-1-甲基吡嗪-2(1H)-酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到5-chloro-3-(ethylamino)-1-methyl-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

文献信息

• 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.