1-benzyl-5-bromo-3-methoxy-6-methyl-2(1H)-pyrazinone | 853687-90-8

• 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: 1-benzyl-5-bromo-3-methoxy-6-methyl-2(1H)-pyrazinone
• 英文别名: 1-Benzyl-5-bromo-3-methoxy-6-methylpyrazin-2-one；1-benzyl-5-bromo-3-methoxy-6-methylpyrazin-2-one
• CAS: 853687-90-8
• 化学式: C₁₃H₁₃BrN₂O₂
• 分子量: 309.162
• InChiKey: UUYURVRBHZOKFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-bromo-3-methoxy-6-methyl-2(1H)-pyrazinone 、 3-噻吩硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.0h， 以95%的产率得到1-benzyl-3-methoxy-6-methyl-5-(3-thienyl)-2(1H)-pyrazinone
  参考文献：
  名称：

  Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions

  摘要：

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.056
• 作为产物：
  描述：

  1-benzyl-5-chloro-3-methoxy-6-methyl-2(1H)-pyrazinone 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-benzyl-5-bromo-3-methoxy-6-methyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions

  摘要：

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.056

文献信息

• Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions
  作者：Rasha Azzam、Wim M. De Borggraeve、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/j.tet.2005.02.056

  日期：2005.4

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.