4,5-bis(N-tert-butylaminocarbonyl)-2-methylpyridazin-3(2H)-one | 1395895-75-6

• 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: 4,5-bis(N-tert-butylaminocarbonyl)-2-methylpyridazin-3(2H)-one
• 英文别名: 4-N,5-N-ditert-butyl-1-methyl-6-oxopyridazine-4,5-dicarboxamide
• CAS: 1395895-75-6
• 化学式: C₁₅H₂₄N₄O₃
• 分子量: 308.381
• InChiKey: YXANKMPLGQSAOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 叔丁胺 、 4,5-二溴-2-甲基-2H-吡嗪-3-酮 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 以73%的产率得到4,5-bis(N-tert-butylaminocarbonyl)-2-methylpyridazin-3(2H)-one
  参考文献：
  名称：

  Functionalization of the pyridazin-3(2H)-one ring via palladium-catalysed aminocarbonylation

  摘要：

  5-Iodo- and 4,5-dibromo-2-methylpyridazin-3(2H)-ones were aminocarbonylated in the presence of various amines including amino acid methyl esters in a palladium-catalysed reaction. The iodo derivative afforded the corresponding amides with complete conversion and high isolated yields. The dibromo derivative has shown unexpectedly high reactivity in this reaction, resulting in 4,5-dicarboxamides using primary amines as N-nucleophiles. Monoaminocarbonylation has not been observed, i.e., neither 4-bromo-5-carboxamide nor 4-carboxamido-5-bromo derivatives have been formed. However, the use of secondary amines such as piperidine and morpholine resulted in the formations of mixtures of amino-substituted bromopyridazinones. That is, no carbon monoxide insertion took place in these cases. Some mechanistic details of the formation of aminocarbonylation and amination products are also discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.030